Hydrochloric Acid → HCID 57659766, compound

Participants

Reaction Conditions

Reaction Steps

(2S)-tert-Butyl 2,5-dicyclopropyl-3-oxopyrrolidine-1-carboxylate (20) (127 mg, 0.480 mmol) was placed in dioxane (0.5 mL) and treated with 4N HCl in dioxane (2.0 mL). When reaction was done as indicated by TLC monitoring, it was concentrated in vacuo and used without further purification. This material was dissolved in CH2Cl2 (3 mL) and placed under nitrogen. DMAP (12 mg, 0.096 mmol) and Et3N (0.20 mL, 1.44 mmol) were added and the reaction cooled to 0° C. 4-(Trifluoromethyl)benzene-1-sulfonyl chloride (129 mg, 0.528 mmol) was added and the reaction stirred for 16 hr warming from 0° C. to rt. The reaction was concentrated in vacuo and the resulting crude product was purified by column chromatography using EtOAc/hexane gradients to yield (2S)-2,5-dicyclopropyl-1-(4-(trifluoromethyl)phenylsulfonyl)pyrrolidin-3-one (21) (149 mg, 83% over two steps) as a 58:42 mixture of diastereomers. The product was a clear oil that solidified upon standing. MS (m/z) 374.1 (M+H)+; retention time (210 nM)=8.329 and 8.500 min, method [7].

Provenance & Evidence