Ethanol → HCID 12393700, compound

Participants

Reaction Steps

In 10 ml. of ethanol is suspended 100 mg. of sodium borohydride and, under stirring, is added 200 mg. of 6-benzyloxy-5-formyl-2-isopropylamino-3,4-dihydro-1(2H)-naphthalenone hydrochloride. The mixture is agitated at room temperature for 2 hours, after which time a saturated solution of sodium chloride and ethyl acetate was added. The ethyl acetate layer is taken, washed with a saturated aqueous solution or sodium chloride and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure and the residue is recrystallized from ethyl acetate-ethanol. The above procedure provides trans-6-benzyloxy-1-hydroxy-5-hydroxymethyl-2-isopropylamino-1,2,3,4-tetrahydronaphthalene as white crystals. Yield 128 mg.; melting point: 138°-139° C.

Provenance & Evidence