HCID 13296325, compound → HCID 71230571, compound

Participants

Reaction Steps

A mixture of (S)-4-benzyl-3-((1S,6S)-4,6-dimethylcyclohex-3-enecarbonyl)oxazolidin-2-one (6 g, 19.1 mmol) and 10% Pd/C (500 mg) in EtOH (50 mL) under a H2 atmosphere (1 atm) was stirred at room temperature overnight. The reaction mixture was filtered through a pad of diatomaceous earth and concentrated to give a 3:1 mixture of diastereomers, which were separated by preparative chiral column chromatography (Chiralcel OD-H (20 cm×250 cm; semi prep): Retention time: 24 min, 33 min (major) (80:20 heptane:ethanol)), providing (S)-4-benzyl-3-((1S,2S,4S)-2,4-dimethylcyclohexanecarbonyl)oxazolidin-2-one (2.3 g, 38%).

Provenance & Evidence