Hydrochloric Acid → (S)-1-(4-chlorobenzyl)-3-hydroxypyrrolidin-2-one

Participants

Reaction Steps

A solution of 4 M HCl in dioxane (4.93 ml, 19.7 mmol) was added to a stirred solution of (S)-3-((tert-butyldimethylsilyl)oxy)-1-(4-chlorobenzyl)pyrrolidin-2-one (1.34 g, 3.94 mmol) in dichloromethane (4 mL) at RT. The reaction mixture was stirred for 2 h. The reaction mixture was concentrated in vacuo to afford (S)-1-(4-chlorobenzyl)-3-hydroxypyrrolidin-2-one (910 mg, 4.03 mmol, quantitative yield): LC-MS (M+H)+ 226.1; 1H NMR (500 MHz, methanol-d4) δ 7.37-7.33 (m, J=8.5 Hz, 2H), 7.27-7.23 (m, J=8.5 Hz, 2H), 4.52-4.37 (m, 2H), 4.34 (t, J=8.2 Hz, 1H), 3.30-3.18 (m, 2H), 1.84 (dq, J=12.8, 8.5 Hz, 1H).

Provenance & Evidence