Benzyl Alcohol → Benzyl oxolan-3-ylcarbamate

Participants

Reaction Steps

A mixture of 3-tetrahydrofuroic acid (3.5 gm, 30 mmol), diphenylphosphorylazide (6.82 ml, 32 mmol), triethylamine (5 ml, 36 mmol) in dioxane (35 ml) was stirred at room temperature for 20 minutes, then heated in a 100° C. oil bath under dry nitrogen for 2 hours. Benzyl alcohol (4.7 ml, 45 mmol) was then added, and heating was continued at 100° C. for 22 hours. The mixture was cooled, filtered, and filtrate concentrated under reduced pressure. The residue was dissolved in 2N HCl and extracted twice with ethyl acetate. The extracts were combined and washed with water, then sodium bicarbonate, and finally brine, and dried over magnesium sulfate. The product was concentrated under reduced pressure to an oil. The oil was chromatographed on silica gel, eluting with 30% to 60% ethyl acetate/hexanes, to give 3.4 g of N-benzyloxycarbonyl-3-aminotetrahydrofuran as an oil.

Provenance & Evidence