Benzyl Alcohol → Benzyl [(1S)-1-(4-methoxyphenyl)ethyl]carbamate

Participants

Reaction Steps

To a stirred solution of the above acid (28) (29.87 g) in dry toluene (300 mL) at room temperature fitted with a reflux condenser under Ar was added triethylamine (26 mL) followed by diphenylphosphorylazide (38 mL). The reaction was then placed into an oil bath at 80° C. and stirred till gas evolution ceased (~30 min). Benzyl alcohol (17 mL) was next added and the reaction stirred for 3 h at 80° C., evaporated, taken up in ethyl acetate, washed with aqueous 1N Na2CO3, aqueous 1N HCl, saturated NaCl, dried over MgSO4 and evaporated. The product (29) was obtained by flash chromatography on silica gel eluted with 20% ethyl acetate in n-hexane. (42.87 g, 91%): TLC Rf 0.36 (CHCl3) Rf 0.39 (20% ethyl acetate, n-hexane).

Provenance & Evidence