Water → HCID 46198683, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(3-amino-3-methylbutyl)-1-azoniabicyclo[2.2.2]octane methanesulfonate hydrochloride (0.31 g, 1.2 mmol) in methanol (4.5 mL) was cooled in an ice bath for 15 min. t-BuOCl (0.41 mL, 3 equiv, 3.48 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., and 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 concentrated via rotovap with the water bath set at 25° C. to give a white solid, (0.21 g, 58.9%). 1H NMR (D2O, 400 MHz): δ 1.43 (s, 6H), 1.96-2.03 (m, 6H), 2.16-2.25 (m, 3H), 2.82 (s, 3 H), 3.21-3.29 (m, 2H), 3.40-3.46 (m, 6H). LRMS (ESI+) for C12H23Cl2N2+ (265.1); Found: 265, 267 (M+, M2H+).

Provenance & Evidence