Sodium Methoxide → HCID 54082073, compound

Participants

Reaction Steps

7 N-(Benzyloxycarbonyl)-2,3-bis(benzoyloxymethyl) cyclopropylamine (0.22 g, 479 mmol) from Step F was dissolved in 5 mL of methanol. Sodium methoxide (52 mg, 95.9 mmol) was added to this solution and the reaction mixture was stirred at ambient temperature for 0.5 h. TLC analysis (on silica gel plates eluted with 10% methanol in chloroform) indicated that the starting material had been consumed in the reaction. The reaction mixture was concentrated in vacuo and the residue dissolved in water. The aqueous solution was acidified with Amberlite® IR-120(plus) acidic ion exchange resin. The resin was removed by filtration and the filtrate concentrated in vacuo. The residue was purified by column chromatography on a 2×20 cm silica gel column eluted with 5% methanol in methylene chloride. Fractions numbered 9 -14 were combined and concentrated in vacuo to give 51 mg (33.3% yield) of N-benzyloxycarbonyl 2,3-bis(hydroxymethyl) cyclopropylamine. DCI NH3MS, M/Z: 252 (M+H)+, 269 (M+NH4)+. 1H NMR (CDCl3) 1.10 (m, 1H, 1.40 (m, 1H), 1.59 (s, O-H), 2.60 (dd, 1H), 2.75 (N-H), 3.31 (ddd, 2H), 3.77 (dd, 1H), 4.00 (dd, 1 H), 5.12 (s, 2H), 7.32 (m, 5H) ppm.

Provenance & Evidence