Formic Acid → HCID 57949399, compound

Participants

Reaction Steps

To a solution of 7-chloro-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbaldehyde (60 mg, 0.162 mmol) in methanol (1.6 mL) was added formic acid (0.02 ml), 4-Aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (35 mg, 0.162 mmol), and Sodium cyanoborohydride (0.2 mL, 1M in THF) respectively. The mixture stirred at room temperature for 1 hour and was then diluted with water and extracted with ethyl acetate. The organic were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography (56-60% ethyl acetate in hexanes) provided the title compound (47 mg, 52%). 1H NMR (300 MHz, CDCl3): δ (7.35 (d, 4H), 7.18 (d, 2H), 4.77 (s, 2H), 4.25 (s, 2H), 4.13 (br s, 1H), 3.86 (s, 2H), 2.65 (t, 4H), 2.54 (d, 2H), 1.70 (t, 4H), 1.45 (s, 9H)

Provenance & Evidence