Methanol → Diisopropyl Ether

Participants

Reaction Steps

The solution of 3.10 g of tert-butyl {3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]4-methyl-1(S)-(R)-oxiranylpentyl}carbamate (Example 1b) in 64 ml of methanol is admixed with 1.04 g of sodium azide and 0.62 g of ammonium chloride and stirred at reflux over 6 hours. The reaction solution is cooled, poured onto ice-water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed successively with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) and subsequent crystallization (diisopropyl ether) as white crystals. Rf=0.29 (1:2 EtOAc-heptane); Rt=21.60 (gradient II). m.p. 98-99° C.

Provenance & Evidence