Hydrochloric Acid → (3R,5S)-5-(Methoxycarbonyl)pyrrolidin-3-yl 4-vinyl-1,3-dihydro-2H-isoindole-2-carboxylate Hydrochloride

Participants

Reaction Steps

A solution of 1-tert-Butyl 2-methyl (2S,4R)-4-{[(4-vinyl-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboxylate (13.9 g, 33.4 mmol) in ethyl acetate (700 mL) was cooled in an ice bath the saturated with hydrogen chloride gas. The reaction flask was sealed and allowed to warm to room temperature. After 3.5 h the solvent was removed by evaporation to give the title compound as a gray solid, 11.2 g, 95% yield). 1H NMR (500 MHz, ppm, CD3OD) δ 7.47-7.45 (m, 1 H), 7.32-7.31 (m, 1 H), 7.26-7.21 (m, 1 H), 6.79-6.73 (m, 1 H), 5.79-5.73 (m, 1 H), 5.46 (s, 1 H), 5.41-5.38 (m, 1 H), 4.80-4.72 (m, 4 H), 3.91 (s, 3 H), 3.74-3.63 (m, 2 H), 2.77-2.71 (m, 1 H), 2.51-2.46 (m, 1 H), LRMS (ESI) m/z 317 [(M+H)+; calcd for C17H21N2O4: 317].

Provenance & Evidence