Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 16220291, compound

Participants

Reaction Conditions

Reaction Steps

A vigorously stirred slurry of ethyl 1,3-dithiolane-2-carboxylate (8, 1.50 mL, 10.5 mmol) and N,O-dimethylhydroxylamine hydrochloride (2.57 g, 26.2 mmol) in THF (21 mL) was treated dropwise with isopropylmagnesium bromide (52.5 mmol, 26.3 mL, 2 M in THF) over 40 min at −78° C. under argon. The reaction mixture was stirred for 1 h at −78° C. under argon. The reaction mixture was quenched with saturated aqueous NH4Cl/H2O (1:1). The aqueous phase was extracted with ether (3×100 mL). The combined organic extract was washed (water, brine), dried (Na2SO4), concentrated and chromatographed [silica, EtOAc/hexanes (2:1)] to afford a yellow oil that solidified upon storage at 1° C. (985 mg, 49%). The characterization values (1H NMR, 13C NMR, ESI-MS) were consistent with those for the title compound prepared via a different synthetic route.43

Provenance & Evidence