Dimethyl Sulfoxide → Ammonium Hydroxide

Participants

Reaction Steps

A solution of 1.6 ml of DMSO in 4.8 ml of CH2Cl2 was added slowly, under a nitrogen atmosphere and at −55° C., to a solution of 0.9 ml of oxalyl chloride in 21 ml of CH2Cl2. After 2 min. 3.6 g (10.3 mmol) of 3-bromo-4,5-epoxy-17-methylmorphinan-6-ol in 20 ml of CH2Cl2 were added, followed, after 15 min. by 6.6 ml of Et3N. The reaction mixture was allowed to warm up to room temperature in 2 h, then it was quenched with 50 ml of H2O. The phases were separated, the organic phase was dried over NA2SO4 and the solvent was removed in vacuo. The crude reaction mixture was purified by flash chromatography, eluting with a mixture CH2Cl2/MeOH/conc. NH4OH 90:7:0.7 respectively, yielding 2.87 g of the title product.

Provenance & Evidence