Acetic Acid → N-[1-(3-Chlorobenzyl)-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl]-carbamic acid tert-butyl ester

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Reaction Steps

To a solution of (6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl ester (820 mg, 3 mmol), prepared as described in Example 1C, and 3-chloro benzaldehyde (0.34 mL, 3 mmol) in DCE (10 mL) was added NaBH(OAc)3 (1.78 g, 8.4 mmol), followed by acetic acid (0-34 mL, 6 mmol). The reaction was stirred at RT for 16 h, then quenched with saturated aqueous NaHCO3, extracted with CH2Cl2 (30 mL×3). The organic extracts were washed with water, saturated aqueous NaCl, dried (Na2SO4), and concentrated. The resulting residue was chromatographed (silica gel) eluting with EtOAc (10-50%) in hexanes to give the title compound (571 mg, 48%) as a foam.

Provenance & Evidence