Sodium triacetoxyborohydride → 7-Bromo-2-(1-(4-cyanobenzyl)-5-imidazolylmethyl)-1,2,3,4-tetrahydroisoquinoline

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Reaction Steps

To a solution of 7-bromo-1,2,3,4-tetrahydroisoquinoline (0.742 g, 3.5 mmol) in CHCl2CHCl2 (15 mL) was added 1-(4-cyanobenzyl)-5-imidazole carboxaldehyde (0.812 g, 3.85 mmol), 4 Å sieves and NaBH(OAc)3 (1.11 g, 5.25 mmol). The mixture was stirred at room temperature for 16 h. and a further portion of NaBH(OAc)3 (0.55 g, 2.6 mmol) was added. After an additional 24 h the mixture was diluted with EtOAc, filtered through celite, washed with brine, dried (Na2SO4) and concentrated. The residue was stirred in 2N Hcl (50 mL) for 2 h. then extracted with ether. The aqueous layer was basified with 6N KOH and extracted 3× CH2Cl2 which was then washed with brine, dried (Na2SO4) and the solvent evaporated in vacuo. Crystallization from ether afforded the title compound as a white solid.

Provenance & Evidence