Triphenylphosphine → (R)-N,O-bis(phenoxycarbonyl)-N-(3-butyn-2-yl)hydroxylamine

Participants

Reaction Steps

A solution of (2S-trans)-3-methyloxiranemethanol 4-methylbenzenesulfonate (484 mg; 2 mmol), prepared as in step 1, in dry THF (20 ml) was treated at -70° C. to -60° C. with n-BuLi (1.6M in hexane, 7.5 ml, 12 mmol) under an atmosphere of nitrogen. Glacial acetic acid (1 ml) was added after consumption of all the rosylate (monitored by TLC). After 15 min, sodium bicarbonate (600 mg) was added and the reaction mixture was allowed to warm to room temperature. After filtration through Celite, N,O-diphenoxycarbonylhydroxylamine (550 mg, 2.00 mmol) and triphenylphosphine (786 mg, 3.00 mmol) were added to the filtrate. The resulting mixture was treated with DEAD (0.5 ml, 3.0 mmol), taking care that the reaction temperature did not rise above ambient temperature. The reaction mixture was stirred at room temperature for 16 hours and then concentrated in vacuo. The residue was purifed by chromatography on silica-gel (10% ethyl acetate/hexane) to give (R)-N,O-bis(phenoxycarbonyl)-N-(3-butyn-2-yl)hydroxylamine(contaminated with phenol).

Provenance & Evidence