Sodium triacetoxyborohydride → 7-{2-Oxo-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

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Reaction Steps

A solution of 7-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (100 mg, 0.39 mmol) in 10 mL of anhydrous DCM was added (1-Oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (69 mg, 0.39 mmol), NaBH(OAc)3 (330 mg, 1.56 mmol) and the mixture was stirred at room temperature overnight. DCM was added, and the mixture was washed with brine. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give the desired product. 1H-NMR (400 MHz, CDCl3) δ ppm 7.79 (d, J=7.5 Hz, 1H), 7.27-7.35 (m, 4H), 7.12 (d, J=8.3 Hz, 1H), 5.23 (s, 2H), 4.74-4.85 (m, 1H), 3.17-3.34 (m, 4H), 2.64-2.95 (m, 10H), 1.74-1.95 (m, 2H).

Provenance & Evidence