5-[2-[(Butylamino)carbonyl]-3-methyl-1-butenyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester → 5-[2-[(Butylamino)carbonyl]-3-methylbutyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester

Participants

Reaction Steps

A THF (2.03 mL) solution containing 5-[2-[(butylamino)carbonyl]-3-methyl-1-butenyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester (236 mg, 0.51 mmol) and rhodium on alumina (24 mg, 10% by wt, 5% Rh content) was placed under a hydrogen atmosphere for 16 h. Additional rhodium on alumina (24 mg) in THF (2.03 mL) was added and the reaction continued under H2 atmosphere for 6 h. The mixture was diluted with CHCl3, filtered and concentrated in vacuo. Silica gel chromatography (3:1 to 3:2 hexane:Et2O gradient) of the concentrate afforded the title compound (171 mg, 70%). MS (ESI) m/e 465 (M-H)-MS (ESI) m/e 467 (M+H)+.

Provenance & Evidence