Sodium cyanoborohydride → 2-[1-(3-Ethoxy-4-methyl-benzyl)-piperidin-4-yl]-2,3-dihydro-isoindol-1-one

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Reaction Steps

To a solution of 2-piperidin-4-yl-2,3-dihydro-isoindol-1-one trifluoroacetate (164.0 mg, 0.27 mmol, 1.0 equiv; 36% purity according to mass balance in preceeding step) in isopropanol (3.4 mL) was added 3-ethoxy-4-methyl-benzaldehyde (44.8 mg, 0.27 mmol, 1.0 equiv; intermediate B19), titanium tetra-isopropoxide (232.8 mg, 0.82 mmol, 3.0 equiv) and sodium cyanoborohydride (34.3 mg, 0.55 mmol, 2.0 equiv). The reaction mixture was allowed to react overnight and then poured directly onto a silica column. Eluting with ethyl acetate/triethylamine (98:2) yielded 29.0 mg (29%) of the title compound as white crystals. MS (ISP): 365.1 [M+H]+.

Provenance & Evidence