tert-Butyldimethylsilyl chloride → HCID 66877225, compound

Participants

Reaction Steps

t-Butyldimethylchlorosilane (116.55 mg, 0.773 mmol), TEA (0.1336 mL, 0.975 mmol) and DMAP (9 mg, 0.0736 mmol) were added to a solution of (S)-3-[4-(4-hydroxy-benzenesulfonyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (297 mg, 0.736 mmol) in DCM (5 mL) under argon atmosphere. The reaction mixture was stirred at room temperature for 3 hours. and then a solution of 10% KHSO4/Na2SO4 was added. The mixture was extracted with DCM, and the combined organic extracts were washed with NaHCO3 (10% aqueous solution), dried over Na2SO4, filtered, and evaporated under reduced pressure. The resulting crude material was purified via flash chromatography (hexane/EtOAc, 783/17) to give 370.6 mg (97% yield) of (S)-3-{4-[4-(tert-butyl-dimethyl-silanyloxy)-benzenesulfonyl]-phenyl}-pyrrolidine-1-carboxylic acid tert-butyl ester as a foam.

Provenance & Evidence