Cyclopropylamine → HCID 118307040, compound

Participants

Reaction Steps

A mixture of 2-(but-3-en-1-yl)-4-fluorobenzaldehyde (50 mg, 0.281 mmol) and cyclopropanamine (16.02 mg, 0.281 mmol) in MeOH (2 mL) was stirred at rt for 30 min. Sodium borohydride (5.31 mg, 0.140 mmol) was added and stirred at rt for 1 h. It was then quenched with NH4Cl, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by biotage, eluting with 25% EtOAc/hexane to isolate N-(2-(but-3-en-1-yl)-4-fluorobenzyl)cyclopropanamine (20 mg, 0.091 mmol, 32.5% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.26 (dd, J=8.3, 6.1 Hz, 1H), 6.93-6.82 (m, 2H), 5.95-5.84 (m, 1H), 5.13-5.00 (m, 2H), 3.83 (s, 2H), 2.81-2.75 (m, 2H), 2.41-2.33 (m, 2H), 2.18 (tt, J=6.6, 3.5 Hz, 1H), 0.51-0.44 (m, 2H), 0.43-0.35 (m, 2H).

Provenance & Evidence