Benzyl Alcohol → Benzyl [1-(4-nitrobenzyl)but-3-enyl]carbamate

Participants

Reaction Steps

In the presence of triethylamine (5.6 ml, 40.0 mmol) and benzyl alcohol (5.18 g, 48.0 mmol) in toluene, 11.55 g (42.0 mmol) of phosphoric acid diphenyl ester azide are added at 50° C. to 2-(4-nitro-benzyl)-pent-4-enecarboxylic acid [2-(4-nitro-benzyl)-pent-4-enoic acid is prepared analogously to 2-(4-chloro-benzyl)-pent-4-enoic acid, see J. Med. Chem, 1968, 11(3), 5341 (9.3 g, 40.0 mmol). After 20 minutes the temperature is increased slowly and the mixture is then maintained under reflux for 3 hours. After cooling, the reaction mixture is washed twice with 1 N sodium hydroxide solution, twice with 1 N hydrochloric acid and twice with brine, dried over sodium sulfate and concentrated by evaporation using a rotary evaporator. After crystallisation of the crude product from toluene/hexane, the title compound is obtained in the form of white crystals. M.p.: 94-95° C. TLC: ethyl acetate/hexane (1:3) Rf =0.22.

Provenance & Evidence