Tetrabutylammonium Fluoride → 3-(4-Mercapto-2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

A solution of tetrabutylammoniumfluoride (1.0 M in THF, 9.3 mL) was added to a solution of 3-[2-methoxy-4-(2-trimethylsilanyl-ethylsulfanyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.380 g, 0.9275 mmol) in THF (5 mL) and the reaction mixture was stirred at room temperature for 30 minutes. A solution of 10% KHSO4/Na2SO4 was added and the resulting mixture was extracted 3 times with EtOAc. The combined organic extracts were washed with water and brine; and then dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude material was purified via flash chromatography (hexane/EtOAc/AcOH, 80/20/0.1) to give 0.178 g (62% yield) of 3-(4-mercapto-2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a clear oil.

Provenance & Evidence