Acetone → HCID 12393679, compound

Participants

Reaction Steps

In a mixture of 15 m. acetone and 20 ml. methanol is dissolved 450 mg. of trans-2-amino-6-benzyloxy-5-cyano-1-hydroxy-1,2,3,4-tetrahydronaphthalene hydrochloride and, while nitrogen gas is introduced, 150 mg. of the adduct of lithium cyanoborohydride-dioxane complex is added in small portions at 5°-10° C. After stirring for 2 hours, a saturated aqueous solution of sodium chloride is added and the mixture is extracted with ethyl acetate. The ethyl acetate layers are washed with a saturated aqueous solution of sodium chloride and dried. The solvent is distilled off under reduced pressure and the residue is recrystallized from ethanol-ethyl acetate. The procedure yields white crystals of trans-6-benzyloxy-5-cyano-1-hydroxy-2-isopropylamino-1,2,3,4-tetrahydronaphthalene. This compound is in agreement with the sample according to the prcedure of Example 3. Yield 297 mg.

Provenance & Evidence