Citric Acid → tert-Butyl-7-(1-cyano-2-phenylethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Reaction Steps

To a suspension of 0.178 mmol of (Z)-tert-butyl-7-(1-cyano-2-phenylvinyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate in 2 ml ethanol were added at 0° C. 0.178 mmol of sodium borohydride. The mixture was allowed to warm to room temperature and stirred for 3 d. The mixture was poured on ice water and citric acid (5%) was added until acidic. The aqueous phase was extracted with EtOAc. The combined organic phase was washed with brine, dried over MgSO4, and filtered. Evaporation of the solvent gave 61.2 mg (95%) of a crude slightly yellow oil, that was directly submitted to Boc deprotection.

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