Cyclopropylamine → HCID 118307103, compound

Participants

Reaction Steps

A mixture of cyclopropanamine (40.0 mg, 0.700 mmol), (S)-4-methyl-2-(pent-4-en-2-yloxy)benzaldehyde (130 mg, 0.636 mmol) in MeOH (5 mL) was stirred at rt for 0.5 h. Sodium borohydride (12.04 mg, 0.318 mmol) was then added and the reaction was stirred at rt for 2 h. It was then quenched with water, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by biotage, eluting with 20% EtOAc/hexane to isolate (S)—N-(4-methyl-2-(pent-4-en-2-yloxy)benzyl)cyclopropanamine (20 mg, 0.082 mmol, 12.81% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.12 (d, J=7.8 Hz, 1H), 6.77-6.67 (m, 2H), 5.90 (ddt, J=17.2, 10.2, 7.1 Hz, 1H), 5.20-5.07 (m, 2H), 4.51 (sxt, J=6.0 Hz, 1H), 3.86-3.69 (m, 2H), 2.60-2.39 (m, 2H), 2.34 (s, 3H), 2.12-2.02 (m, 1H), 1.36 (d, J=6.1 Hz, 3H), 0.48-0.32 (m, 4H).

Provenance & Evidence