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20th June 2012 @ 02:11
Resolution of MNR26-5 with (+)-dibenzoyl-D-tartaric acid (MNR5-1)

MNR30-1%20scheme.png

Hazard and Risk Assessment:
As for MNR2-1

Procedure
MNR26-5 (EtOAc extraction minus oil that had crashed out) (1.82 g, 6.94 mmol) and MNR5-1 (2.67 g, 6.94 mmol) was dissolved in IPA (15 mL) and water (3 mL) with heating. All the reagents went into solution and the mixture was left to stand. After standing overnight at room temperature the solution has formed a solid gel. IPA (15 mL) was added and the flask stored in the fridge for 2 hours then at room temperature overnight. The solid was filtered and washed with IPA and hexane to give a just off white solid (1.667 g). The solid was redissolved in IPA (25mL) and water (3 mL) and left to stand at room temperature for 3 hours, solid filtered and washed with hexane. Dissolved in sodium carbonate solution and extracted with EtOAc (25 mL x 3), dired, filtered and concentrated to give a sticky white solid (0.171 g, 0.65 mmol, 9 %)

1H NMR
mnr30-7_1H.pdf

13C NMR
mnr30-7_13C.pdf

Chiral HPLC - 99% ee using the CHIRALCEL OD-H column and a flow rate of 0.5 mL/min
mnr30-7_scaleup.pdf

Chiral HPLC of racemic MNR26-1 using the CHIRALCEL OD-H column and a flow rate of 0.5 mL/min. Peaks at 41 and 44 mins
mnr26-1 15EtOH 05mL_120412.pdf
Attached Files
mnr30-7_1H.pdf
mnr30-7_13C.pdf
MNR30-7.zip
mnr30-7_scaleup.pdf
mnr26-1 15EtOH 05mL_120412.pdf