Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 10538260, compound

Participants

Reaction Steps

A solution of trimethylsilyldiazomethane in ether (2M, 9 mL) was added dropwise to a stirred, ice-bath cooled, mixture of 1-Boc-L-azetidine-2-carboxylic acid (3 g, 15 mmol), dichloromethane (20 mL) and methanol (5 mL) until yellow colour persisted. The mixture was concentrated in vacuo. The residue was treated with THF (30 mL) and N,O-dimethylhydroxylamine hydrochloride (2.04 g; 20.9 mmol) and cooled to 0° C. i-Propylmagnesium chloride in THF (2 M, 22.4 ml, 44.7 mmol) was added dropwise to the mixture and it was stirred for 30 min. After quenching with saturated aqueous NH4Cl (25 ml) and concentrated NH3 (25 ml), the mixture was extracted into ethyl acetate (150 mL). The organic extract was dried (Na2SO4) and concentrated. The residue was purified on silica gel (hexanes-ethyl acetate 0-100%) to give the title product (2.73 g, 75%). 1H NMR (500 MB, CDCl3): δ 5.03 (1H, m), 4.05 (1H, m), 3.87 (1H, m), 3.71 (3H, s), 3.22 (3H, s), 2.46 (1H, m), 2.13 (1H, m), 1.43 (9H, s).

Provenance & Evidence