Sodium Hydroxide → HCID 70567393, compound

Participants

Reaction Steps

Sodium borohydride (0.38 g, 10.04 mmol) was added to a 3-necked flask fitted with a dropping funnel and a condensor. Under a nitrogen atmosphere, a solution of 20 mg of NaOH in 10 ml of methanol was added to the flask and the mixture stirred while a solution of 17-cyclopropylmethyl-3-hydroxy-14-methoxy-8α-methylmorphinan-6-one (31) (0.188 g, 0.528 mmol) in 10 ml of methanol was added dropwise. At this point the reaction mixture was stirred for four hrs. whereupon the reaction was quenched by the addition of 8 ml of 2 N HCl and heating in an oil bath for 10 minutes. The solvent was removed under reduced pressure, then 15 ml of methanol and 10 ml of water were added and the methanol removed under reduced pressure. This step was repeated whereupon the aqueous solution was made basic with solid Na2CO3. A white precipitate formed which was filtered off and the filtrate was extracted with chloroform (4×20 ml). The organic layer was separated, dried over Na2SO4 and concentrated to leave a gummy residue. The residue was chromatographed on silica gel and eluted with methanol:chloroform (50:50) containing a drop of NH4OH to give the free base of (34) upon evaporation of the solvent. The free base was dissolved in chloroform and treated with ethereal HCl to give 17-cyclopropylmethyl-14-methoxy-8α-methylmorphinan-3,6-diol hydrochloride (34) as a colorless solid (0.1 g, 48% theory).

Provenance & Evidence