Trifluoromethanesulfonic anhydride → HCID 46946219, compound

Participants

Reaction Steps

To a solution of 1-phenyl-2,2,2-trifluoroethanol (0.4 mmole) in dichloromethane (1.4 ml) was added at −50° C. diisopropylethyl amine (2.0 mmole) and triflic anhydride (0.42 mmole) and stirring was continued at −50° for 1 h. To the mixture was added at −50° C. a solution of (2S,4R)-4-benzenesulfonyl-pyrrolidine-2-carboxylic acid cyanomethyl-amide hydrochloride (0.4 mmole) prepared in analogy to experiment K1 in dichloromethane (0.4 ml) and stirring was continued at 22° C. for 2 d. The mixture was partitioned between ethyl acetate and water, the organic layer was dried, evaporated and the residue was chromatographed on silica to give (2S,4R)-4-benzenesulfonyl-1-(2,2,2-trifluoro-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid cyanomethyl-amide as a colorless solid. MS: 452.1 [M+H]+.

Provenance & Evidence