Tert-Butyl hypochlorite → HCID 46198844, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(3-amino-3-methylbutyl)-1-methylpyrrolidinium chloride hydrochloride (1.07 g, 4.4 mmol) in a mixture of methanol (15 mL) and water (10 mL) was cooled in an ice bath for 15 min. t-BuOCl (1.56 mL, 3 equiv, 13.2 mmol) was added in one portion via syringe to the colorless solution to give a deep yellow solution. The reaction mixture was stirred for 30 min at 0° C., then concentrated under reduced pressure to yield a colorless oil. This oil was dissolved into water and purified via reverse phase chromatography on a Shimadzu Prep-LC utilizing water/acetonitrile and 0.05% acetic acid as modifier. Fractions were collected monitoring UV absorbance at 215 nm. Fractions were pooled and lyophilized to give a pale yellow foam, (0.94 g, 77.6%). 1H NMR (D2O, 400 MHz): δ 1.44 (s, 6H), 2.17 (m, 4H), 2.17-2.32 (m, 2H), 3.06 (s, 3 H), 3.45-3.60 (m, 6H). LRMS (ESI+) for C10H21Cl2N2+ (239.1); Found: 239, 241 (M+, M2H+).

Provenance & Evidence