3-Fluorobenzaldehyde → HCID 16039596, compound

Participants

Reaction Steps

To a solution of 2-Cyclopropylmethyl-7-methyl-5-piperidin-4-ylmethyl-2,3-dihydro-isoindol-1-one (30 mg, 0.110 mmol) in methanol (2 mL) was slowly added acetic acid (1 mL). After stirring at room temperature for 5 minutes, 3-Fluoro-benzaldehyde (12.8 μL, 0.121 mmol) and sodium cyanoborohydride (8 μL, 0.111 mmol) were added dropwisely. The mixture stirred at room temperature for 2 hours and was neutralized with saturated sodium bicarbonate (10 mL). The aqueous mixture was extracted with dichloromethane and the organics were dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography (10-40% ethyl acetate in hexanes) provided the title compound as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.70-7.23 (m, 1H), 7.09-7.03 (m, 3H), 6.97-6.92 (m, 2H), 4.41 (s, 2H), 3.48-3.44 (m, 4H), 2.88-2.85 (d, 2H), 2.71 (s, 3M), 2.60-2.57 (d, 2H), 1.93 (t, 2H), 1.64-1.50 (m, 3H), 1.36-1.28 (m, 2H), 1.04 (m, 1H), 0.60-0.55 (m, 2H), 0.34-0.32 (m, 2H)

Provenance & Evidence