Benzyl Alcohol → Benzyl [(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]methylcarbamate

Participants

Reaction Steps

A solution of 5.25 g intermediate from Step A above, 8.88 g diphenylphosphoryl azide, and 3.34 g triethyl amine in 100 mL toluene was refluxed under nitrogen for 75 minutes. Benzyl alcohol (2.92 g) was added and reflux continued for additional 15 hours. The reaction mixture was cooled, diluted with ethyl acetate, washed with 5% NaHCO3 and saturated brine, dried over anhydrous Na2SO4, and evaporated under vacuum to give a crude product. It was purified on silica gel with 20˜45% ethyl acetate in hexanes to give the title compound as a yellow oil. 1H NMR (CDCl3, 500 MHz) δ 7.33˜7.40 (m, 5H), 5.175 (d, J=12.1 Hz, 1H), 5.11 (d, J=11.9 Hz, 1H), 4.50˜4.52 (m, 1H), 3.69˜3.75 (m, 1H), 3.60˜3.66 (m, 1H), 1.59 (s, 3H), 1.57 (s, 3H).

Provenance & Evidence