Tetrabutylammonium Fluoride → HCID 58748342, compound

Participants

Reaction Conditions

Reaction Steps

91.1 To a stirred solution of 150 mg (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (example 17.2) at r.t. in 3.3 ml DMF under an argon atmosphere was added 1.71 ml tetrabutylammonium fluoride solution (1 M in THF). The mixture was heated to 80° C. and stirring at that temperature was continued for 19 h. The mixture was cooled to r.t., diluted with EtOAc and washed with H2O. The aqueous phase was back extracted with EtOAc. The combined organics were washed with H2O and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; cyclohexane->cyclohexane/EtOAc 1:1) to give 44 mg (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-2-fluoromethyl-pyrrolidine-1-carboxylic acid tert-butyl ester as off-white amorphous solid. MS 361.0 ([M−H]−)

Provenance & Evidence