Triethylamine → HCID 69435132, compound

Participants

Reaction Steps

A solution of 615 mg (2.19 mmol) (2R,4R)-3-[4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-yl]-propan-1-ol and 0.34 ml (2.40 mmol) triethylamine in 5 ml CH2Cl2 was cooled to −10° C. and treated slowly with 0.31 ml (2.29 mmol) butylchloroformate. After 20 min at this temperature the reaction was extracted with cold (0° C.) aqueous 10% KHSO4/Et2O (3×). The organic phase was washed with aqueous saturated NaHCO3 dried over Na2SO4 and evaporated. Flash column chromatography on silica gel with hexane/EtOAc (2:1 to 1:1) gave 340 mg (32%) of (2R,4R)-2-(3-butoxycarbonyloxy-propyl)-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid butyl ester and 230 mg (28%) of (2R,4R)-2-(3-hydroxy-propyl)-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid butyl ester, MS: 382 (MH+).

Provenance & Evidence