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Synthesis of MNR41-3
Synthesis of MNR40-3 - same reaction time as MNR40-1 but using reagents straight from the bottle and no molecular sievesHIRACHIRAC MNR41.pdfProcedureTo a solution of KAB23-2 (0.10 g, 0.32 mmol) in...
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Preparation of MNR42-1
4-Nitrobenzaldehyde (5.37 g, 35.53 mmol) was suspended in diethyl ether (45 mL). 3,4-Dimethoxyphenylethanamine (6.0 mL, 35 mmol) was added dropwise, with stirring. The mixture was left to stir at...
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Synthesis of MNR41-4 - monitoring by lcms
Synthesis of MNR40-4 - monitoring reaction progress by LCMSHIRACHIRAC MNR41.pdfProcedureTo a solution of MNR42-1 (1.5 g, 4.77 mmol) in dry acetonitrile (160 mL, HPLC stored over 3 Å molecular sieves...
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Yb(OTf)3 catalysed (5 mol%) acyl-PS to give...
START: 18/07/12FINISH: 19/07/12Hazard and Risk AssessmentHazard and Risk Assessment KAB26-4Previous ExperimentsPreparation of MNR42-1Yb(OTf)3 catalysed acyl-PS to give...
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Acyl-PS to give KAB26-13 using Yb(OTf)3 (5 mol%) catalyst solution
START: 18/07/12FINISH: 20/07/12Hazard and Risk AssessmentHazard and Risk Assessment KAB26-4Previous ExperimentsPreparation of MNR42-1Yb(OTf)3 catalysed acyl-PS to give...
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Synthesis of MNR41-5 - monitoring by lcms
After it looked like MNR40-4 went to completion after 1 hour it was decided to monitor the reaction over the first hour. Increasing equivalents of reagents was also investigated.To a solution of...
View ArticleYb(OTf)3 Catalysed Acyl-PS - Summary of Conditions
https://docs.google.com/spreadsheet/ccc?key=0AkBTXODOQY0ldEFpWkYtUjhBeERuOTFLRE9vM0YyZVE#gid=0
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Synthesis of MNR41-6 - monitoring by lcms
Repeat of MNR41-5 but monitoring the reaction for longer.To a solution of MNR42-1 (0.5 g, 1.59 mmol) in dry acetonitrile (50 mL, HPLC grade stored over 3 Å molecular sieves for 24 hours) and 3 Å...
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Yb(OTf)3 catalysed acyl-PS formation of KAB26-14 in THF
START: 23/07/12FINISH: 23/07/12Summary and ConclusionSubstrate scale: 104 mg (to 0.02 M).Yb(OTf)3 loading: 5 mol%.Solvent: THF.Isolated yield: 27% (following chromatography).Hazard and Risk...
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Acyl-PS formation of KAB26-15 using Yb(OTf)3/THF solution
START: 23/07/12FINISH: 23/07/12Summary and ConclusionYb(OTf)3/THF catalyst solution: 36 mM.Substrate scale: 103 mg (to 0.02 M).Yb(OTf)3 loading: 5 mol%.Solvent: THF.Isolated yield: 51% (following...
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Yb(OTf)3 (THF solution) catalysed acyl-PS formation of KAB26-16 in MeCN
START: 23/07/12FINISH: 23/07/12Summary and ConclusionYb(OTf)3/THF catalyst solution: 36 mM.Substrate scale: 100 mg (to 0.02 M).Yb(OTf)3 loading: 5 mol%.Solvent: 1:32, THF/MeCN, v/v.Isolated yield: 97%...
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Yb(OTf)3/PyBOX catalysed asymmetric acyl-PS formation of KAB26-17
START: Scheduled for 25/07/12FINISH: Hazard and Risk AssessmentHRA KAB26-17Previous ExperimentsPreparation of MNR42-1Yb(OTf)3 (THF solution) catalysed acyl-PS formation of KAB26-16 in MeCNChemical...
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Yb(OTf)3/BINOL catalysed asymmetric acyl-PS formation of KAB26-18
START: 25/07/12FINISH: Hazard and Risk AssessmentHRA KAB26-18Previous ExperimentsPreparation of MNR42-1Yb(OTf)3/PyBOX catalysed asymmetric acyl-PS formation of KAB26-17Chemical...
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Yb(OTf)3/BOX catalysed asymmetric acyl-PS formation of KAB26-19
START: 25/07/12FINISH: Hazard and Risk AssessmentHRA KAB26-19Previous ExperimentsPreparation of MNR42-1Yb(OTf)3/PyBOX catalysed asymmetric acyl-PS formation of KAB26-17Chemical...
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Attempts to isolate [Yb(OTf)2(R-iPr-pybox)2]+
Yb(OTf)3 (0.050 g, 0.08 mmol) and R-iPr-box (0.049 g, 0.16 mmol) in THF (5 mL) in THF (5 mL) was stirred at room temperature for 10 minutes. The solution was then concentrated to about 0.5 mL volume...
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Quantifying MNR41 and PZQ as a standard in LCMS analysis - MNR41-7
PZQ was selected as a standard for monitoring the formation of MNR41 due to it's similarity to the product.PZQ was initially investigated at different concentrations to show if it had a linear...
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Yb(OTf)3/BINOL catalysed asymmetric acyl-PS formation of KAB26-20
START: 26/07/12FINISH: 26/07/12Hazard and Risk AssessmentHRA KAB26-18Previous ExperimentsPreparation of MNR42-1Yb(OTf)3/PyBOX catalysed asymmetric acyl-PS formation of KAB26-17Chemical...
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(PyBOX)2-Yb(OTf)3 catalysed asymmetric acyl-PS formation of KAB26-21
START: 26/07/12FINISH: 27/07/12Hazard and Risk AssessmentHRA KAB26-18Previous ExperimentsPreparation of MNR42-1Yb(OTf)3/PyBOX catalysed asymmetric acyl-PS formation of KAB26-17Chemical...
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Synthesis of MNR41-8 @ -30 C
Monitoring reaction at -30 C with the idea that maybe complexes will be more stable at these temperatures and catalyse the reaction ahead of free Yb(OTf)3.To a solution of MNR42-1 (0.2 g, 0.64 mmol) in...
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Synthesis of MNR41-9 @ -5 C
Monitoring reaction at -5 °C with the idea that maybe complexes will be more stable at these temperatures and catalyse the reaction ahead of free Yb(OTf)3.To a solution of MNR42-1 (0.2 g, 0.64 mmol) in...
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Synthesis of MNR41-10 - testing catalyst stored in solution
Repeating the reaction at standard conditions (25 °C over 1 hour) to see if the Yb(OTf)3 is stable enough to be stored in solution.To a solution of MNR42-1 (0.2 g, 0.64 mmol) in dry acetonitrile (20...
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Synthesis of MNR41-11 - using YbCl3
Repeating the reaction at standard conditions (25 °C over 1 hour) but changing the source of Ytterbium to YbCl3.To a solution of MNR42-1 (0.2 g, 0.64 mmol) in dry acetonitrile (20 mL, HPLC grade stored...
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Synthesis of MNR41-12 - catalyst loading of 0.1 mol%
Testing standard reaction conditions (25 °C over 1 hour) with a catalyst loading of 0.1 mol%To a solution of MNR42-1 (0.2 g, 0.64 mmol) in dry acetonitrile (20 mL, HPLC grade stored over 3 Å molecular...
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Synthesis of MNR41-13 -control reaction with no Yb added
Control reaction testing the standard reaction conditions (25 °C over 1 hour) without the addition of catalyst.To a solution of MNR42-1 (0.2 g, 0.64 mmol) in dry acetonitrile (20 mL, HPLC grade stored...
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Synthesis of MNR41-14 -repeat control reaction, metal free
Repeat of MNR41-13 but using a new clean vial to carry out the reaction in. Also, reagents were measure out using a plastic spatula and plastic Gilson tips. The reaction was also shaken on the shaker...
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Synthesis of MNR41-15 -control reaction, no molecular sieves
Repeat of MNR41-14 but leaving out the molecular sieves as they could be slightly acidic.To a solution of MNR42-1 (0.1 g, 0.32 mmol) in HPLC grade acetonitrile (10 mL) and under argon at 0 °C, was...
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Synthesis of MNR41-16 -repeat control reaction, no PZQ
Repeat of MNR41-15 but leaving out the PZQ.To a solution of MNR42-1 (0.1 g, 0.32 mmol) in HPLC grade acetonitrile (10 mL) and under argon at 0 °C, was added was added acetyl chloride (0.041 mL, 0.57...
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Synthesis of MNR44-1
Repeat of MNR41-16 but starting with KAB19-1To a solution of KAB19-1 (0.1 g, 0.37 mmol) in HPLC grade acetonitrile (10 mL) and under argon at 0 °C, was added was added acetyl chloride (0.048 mL, 0.67...
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Synthesis of MNR45-1
Repeat of MNR41-16 but starting with KAB18-1To a solution of KAB18-1 (0.1 g, 0.48 mmol) in HPLC grade acetonitrile (10 mL) and under argon at 0 °C, was added was added acetyl chloride (0.061 mL, 0.86...
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Synthesis of MNR46-1
Repeat of MNR41-16 but starting with KAB22-1To a solution of KAB22-1 (0.1 g, 0.39 mmol) in HPLC grade acetonitrile (10 mL) and under argon at 0 °C, was added was added acetyl chloride (0.05 mL, 0.71...
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Synthesis of SC1-1
Synthesis of SC1-1 from tryptamine and benzaldehyde.SC1-1 was successfully synthesised (1.389 g, 5.594 mmol, 90.0%, m.p. 119 degrees).HIRACSC1-1 and SC2-1 HIRAC.pdfProcedure followed:The synthetic...
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Synthesis of SC2-1
Synthesis of SC2-1 from tryptamine and 4-nitrobenzaldehyde.SC2-1 was successfully synthesised (1.4782 g, 5.040 mmol, 80.4%, m.p. 161-2 degrees).HIRACSC1-1 and SC2-1 HIRAC.pdfProcedure followed:The...
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Synthesis of SC3-1 and SC3-2
Synthesis of SC3-1 and SC3-2 from SC2-1.HIRACSC3-1 and SC3-2 synthesis.pdfProcedure followed:The procedure was identical to that used for MNR41-9, with the following temperature and starting material...
View Articlemnr12-X - duplicate post of KAB8-14
*Duplicate lab book entry to allow data uploadOriginal post - TfOH catalysed PS* reactions to give the dimethoxy PZQ analogues (KAB8-14 & KAB1-5)Acetal MNR10 (0.300 g, 0.66 mmol) was dissolved in...
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Varying The Reaction Conditions of MNR41. MNR41-17, MNR41-18 and MNR41-19
Varying The Reaction Conditions of MNR41. MNR41-17, MNR41-18 and MNR41-19MNR41-17 - no base, no acidMNR41-18 - no base, Yb(OTf)3MNR41-19 - no base, YbCl3Hazard AssessmentHIRAC...
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Attempts To Cyclise MNR42 without AcCl - MNR47-1, MNR47-2, MNR47-3, MNR47-4
Attempts To Cyclise MNR42 without AcCl.MNR47-1 - Yb(OTf)3 and TEAMNR47-2 - Yb(Cl)3 and TEAMNR47-3 - Yb(OTf)3 and lutidineMNR47-4 - Yb(Cl)3 and lutidineHazard AssessmentHIRAC MNR41_47_48.pdfProcedureTo...
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Attempts To Cyclise KAB22-1 without AcCl - MNR48-1, MNR48-2.
Attempts To Cyclise KAB22-1 without AcClMNR48-1 - Yb(OTf)3 and lutidineMNR48-2 - Yb(Cl)3 and lutidineHazard AssessmentHIRAC MNR41_47_48.pdfProcedureTo a solution of KAB22-1 (1eq) in HPLC grade...
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Attempts To Cyclise KAB18-1 using AcCl - MNR45-2, MNR45-3, MNR45-4
Attempts To Cyclise KAB18-1 using AcClHazard AssessmentHIRAC MNR41_47_48.pdfProcedureTo a solution of KAB18-1 (1eq) in HPLC grade acetonitrile (0.03 M) under argon at ambient temperature, was added was...
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Attempts To Cyclise KAB22-1 using AcCl - MNR46-2, MNR46-3, MNR46-4
Attempts To Cyclise KAB22-1 using AcClHazard AssessmentHIRAC MNR41_47_48.pdfProcedureTo a solution of KAB22-1 (1eq) in HPLC grade acetonitrile (0.03 M) under argon at ambient temperature, was added was...
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Attempts To Cyclise KAB22-1 using AcCl and AlCl3 - MNR46-5, MNR46-6, MNR46-7
Attempts To Cyclise KAB22-1 using AcCl and AlCl3 as the lewis acidRef - NEW METHOD FOR SYNTHESIS OF 2-ACYL-1-ARYL-1,2,3,4-TETRAHYDROISOQUINOLINESAuthor: MOLLOV, NM (MOLLOV, NM); VENKOV, AP (VENKOV,...
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Following the Cyclisation of KAB22-1 to MNR46 by LCMS - MNR46-8, MNR46-9,...
The aim over the next few reactions is to compare reaction rate, conversion and yield varying reaction temperature and Yb loadingMNR46-8, 10 mol% Yb at room temperatureMNR46-9, flasks were mixed up...
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Following the Cyclisation of KAB22-1 to MNR46 by LCMS - MNR46-11 and MNR46-12
Aim repeat of the previous reaction but switching the temperatures.MNR46-11, 10 mol% Yb at refluxMNR46-11, stoichiometric Yb at room temperatureHazard AssessmentHIRAC MNR41_47_48.pdfProcedureTo a...
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Synthesis of SC4-1 and SC4-2
Synthesis of SC4-1 and SC4-2 from SC2-1.HIRACSC4 HIRAC.jpegProcedure followed:The procedure was identical to that used for SC3-1 and SC3-1. Reactions were also performed on a 0.1 g scale.SC1-1 (0.1023...
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HPLC Calibrations for MNR46 reactions
Now that it looks like the formation of MNR46 is catalytic (Following the Cyclisation of KAB22-1 to MNR46 by LCMS - MNR46-8, MNR46-9, MNR46-10) it is worth while developing a reliable HPLC method to...
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Re-synthesis of MNR46-13
re-synthesis of MNR46 to try and get a clean sample for characterisation and HPLC analysisHazard AssessmentHIRAC MNR41_47_48.pdfProcedureTo a solution of KAB22-1 (0.60 g, 2.36 mmol) in HPLC grade...
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Attempted Synthesis of MNR46-5
Attempted Synthesis of MNR46-5Hazard AssessmentHIRAC MNR41_47_48.pdfProcedureTo a solution of KAB18-2 (0.29 g, 1.39 mmol) in HPLC grade acetonitrile (14 mL) under argon at 0 °C , was added was added...
View ArticleSynthesis of SC3-3 and SC3-4
Synthesis of SC3-3 and SC3-4 from SC2-1.HIRACRefer to risk/hazard assessment prepared for SC3-1 and SC3-2.3rd October 2012Aim: to repeat SC3-1 and SC3-2.This experiment is a repeat of SC3-1 and SC3-2....
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Synthesis of MNR11-18
As forSynthesis of MNR11-17andSynthesis of MNR11-16Starting material fromPreparation of the dimethoxy Ugi-intermediate (MNR8-5)Hazard and Risk Assessment:HIRAC MNR11.pdfProcedure:To a solution of...
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Hydrolysis of MNR11-18 to give MNR26-7
As forHydrolysis of MNR11-16 to MNR26-4Hydrolysis of MNR11-17 to MNR26-5Starting material fromSynthesis of MNR11-18Hazard and Risk Assessment:HIRAC MNR7.pdfProcedure:MNR11-8 (3.96 g, 10.63 mmol) was...
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