Ammonia → HCID 86751655, compound

Participants

Reaction Steps

A mixture of 1.63 g (25 mmol) of sodium azide, 1.5 ml of water and 10 ml of benzene is treated dropwise with 0.67 ml (12.5 mmol) of concentrated sulphuric acid while cooling with ice (<10°) and stirring. Thereafter, the mixture is cooled to 0°, the benzene phase is decanted off and dried over magnesium sulphate. The thus-obtained nitrogen hydride solution is added to a mixture of 368 mg (1 mmol) of tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(R)-cyclopropylhydroxymethyl]-2,2-dimethyl-3-oxazolidinecarboxylate and 289 mg (1.1 mmol) of triphenylphosphine in 5 ml of benzene. Subsequently, 0.15 ml (1.1 mmol) of diethyl azodicarboxylate is added and the reaction mixture is stirred at room temperature overnight under argon. Thereafter, the reaction mixture is evaporated and, for purification, the residue is chromatographed on 50 g of silica gel using a 3:1 mixture of toluene and ethyl acetate as the eluent. There are obtained 210 mg of tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(S)-cyclopropylazidomethyl]-2,2-dimethyl-3-oxazolidinecarboxylate, MS: 393 (M+H)+, as an oil which gradually crystallizes as well as 130 mg of educt.

Provenance & Evidence