Sodium amide → HCID 86751637, compound

Participants

Reaction Steps

A mixture of 1.4 g (4.3 mmol) of tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (WO 87/05302) and 1.79 g (4.3 mmol) of instantylide, consisting of propyltriphenylphosphonium bromide and sodium amide, in 50 ml of tetrahydrofuran is stirred at room temperature under nitrogen for 30 minutes. Subsequently, the reaction mixture is partitioned between water and ethyl acetate. The organic phase is separated, dried over sodium sulphate and evaporated under reduced pressure. For purification, the residue is chromatographed on 80 g of silica gel using a 1:1 mixture of methylene chloride and petroleum ether as the eluent. There are obtained 900 mg of tert-butyl (4S,5R)-5-[(Z)-1-butenyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate as a resin; MS: 352 (M+H)+.

Provenance & Evidence