Cyclopropylamine → HCID 86751658, compound

Participants

Reaction Steps

A mixture of 733 mg (2.16 mmol) of tert-butyl (4S,5R)-4-(cyclohexylmethyl)-2,2-dimethyl-5-[(RS)-2-oxiranyl]-3-oxazolidinecarboxylate (WO 88/4664) and 2 ml of cyclopropylamine in 15 ml of methanol is stirred at 50° overnight under argon. Thereafter, the reaction mixture is evaporated and, for purification and separation of the epimers, the residue is chromatographed on 100 g of silica gel using a 98:2 mixture of chloroform and methanol as the eluent. There are obtained 185 mg of the less polar tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(S)-2-(cyclopropylamino)-1-hydroxyethyl]-2,2-dimethyl-3-oxazolidinecarboxylate, MS: 397 (M+H)+, and 341 mg of the more polar tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(R)-2-(cyclopropylamino)-1-hydroxyethyl]-2,2-dimethyl-3-oxazolidinecarboxylate, MS: 397 (M+H)+, each as a colourless oil.

Provenance & Evidence