Ammonium Chloride → HCID 69427531, compound

Participants

Reaction Conditions

Reaction Steps

275 mg (0.55 mmol) (2S,4R)-2-azidomethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid butylamide in 8 ml ethanol was treated with 83 mg (2.2 mmol) NaBH4 at 80° C. for 18 h. Additional 175 mg (4.6 mmol) NaBH4 were added in portions, and the reaction was stirred at 80° C. until no starting material could be detected. The solution was poured into a saturated NH4Cl solution, and was extracted with EtOAc, the organic phase was washed with brine, dried over Na2SO4 and evaporated. Column chromatography yielded 213 mg (82%) (2S,4R)-2-aminomethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid butylamide as white foam, which was directly subjected to the following reactions according to reductive amination with 2,5-difluoro-benzaldehyde (example 4a) and subsequent trityl cleavage (method 3) yielding (2S,4R)-2-[(2,5-difluoro-benzylamino)-methyl]-4-mercapto-pyrrolidine-1-carboxylic acid butylamide as colorless oil, MS:358 (MH+).

Provenance & Evidence