Acetic Acid → HCID 54398842, compound

Participants

Reaction Steps

To a suspension of 2b (3.3 g, 5.0 mmol) in a mixture of methanol (50 mL) and THF (30 mL) was added 5 mL of 1 M sodium methoxide in methanol. The reaction mixture was stirred for 5 hours, becoming a clear solution in approximately 30 min. Acetic acid (0.3 mL) was added to neutralize sodium methoxide, and the solution was evaporated to dryness. The residue was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. Chromatography on silica gel, eluting with 5% acetone in CH2Cl2, afforded 1.6 g (85%) of (1S)-2a as a white solid. This product was shown by NMR and CHN analysis to be identical with the racemic material (2a). (1R)-2a was prepared analogously from 2c.

Provenance & Evidence