Ethanol → HCID 6355768, compound

Participants

Reaction Steps

A mixture of (R)-4-benzyl-3-((1R,6R)-4,6-dimethylcyclohex-3-ene-carbonyl)oxazolidin-2-one (1.5 g, 4.8 mmol) (J. Am. Chem. Soc. 110(4), 1988, 1238-1256) in EtOH (24 mL) and 10% Pd/C (500 mg) was stirred under a H2 atmosphere (1 atm) 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: Chiral-Pak AD-H (20 cm×250 cm; semi prep): Retention time: 5.11 min, 6.25 min (80:20 heptane:ethanol), providing the desired compound (R)-4-benzyl-3-((1R,2R,4R)-2,4-dimethylcyclohexanecarbonyl)oxazolidin-2-one (0.65 g).

Provenance & Evidence