Tert-Butyl hypochlorite → HCID 86714589, compound

Participants

Reaction Steps

A solution of 5-(chloromethyl)-5-methylpyrrolidin-2-one (302 mg, 2.05 mmol) in methanol (20 mL) was cooled in ice water for 10 min, before neat tert-butyl hypochlorite (0.46 mL, 4.1 mmol, 2 equiv.) was added in one portion. Additional tert-butyl hypochlorite (0.46 mL, 4.1 mmol, 2 equiv.) was added after 45 min. After 1 h, the mixture was concentrated in vacuo and the residue absorbed on silica. Chromatography on silica (0-2.5% MeOH/DCM) afforded the N-chloro-pyrrolidinone as a colorless oil (292 mg, 78%). 1H NMR (400 MHz, CDCl3) δ 3.74 (d, J=11.9 Hz, 1H), 3.50 (J=11.9 Hz, 1H), 2.66-2.57 (m, 1H), 2.54-2.40 (m, 2H), 2.10-2.01 (m, 1H), 1.43 (s, 3H); 13C NMR (100 MHz, CDCl3) δ171.6 (C), 65.4 (C), 49.1 (CH2), 28.9 (CH2), 27.8 (CH2), 23.1 (CH3); LRMS (ESI/APCI): 182 [M+H]+.

Provenance & Evidence