Reaction #1702054

Reaction equation

(3R)-3-(4-Bromo-phenyl)-cyclopentanone

(1R)-1-(4-fluoro-3-methoxyphenyl)ethylamine hydrochloride

→

title compound

[(1S,3R)-3-(4-Bromo-phenyl)-cyclopentyl]-(1R)-[1-(4-fluoro-3-methoxy-phenyl)-ethyl]-amine

Conditions

Workup

1. 1
   OtherThe product was purified by flash chromatography (gradient of 20-80% EtOAc in heptane containing 2.5% NEt3)
2. 2
   Washthe faster eluting peaks
3. 3
   Otherwere collected

Procedure

General procedure B was followed using (3R)-3-(4-Bromo-phenyl)-cyclopentanone as the ketone and (1R)-1-(4-fluoro-3-methoxyphenyl)ethylamine hydrochloride as the amine. The product was purified by flash chromatography (gradient of 20-80% EtOAc in heptane containing 2.5% NEt3), and the faster eluting peaks were collected to afford the title compound. 1H NMR (300 MHz, CDCl3) δ 7.37 (d, J=8.4 Hz, 2H), 7.10-6.94 (m, 4H), 6.85-6.78 (m, 1H), 3.90 (s, 3H), 3.83 (q, 1H), 3.12-3.00 (m, 1H), 2.96-2.81 (m, 1H), 2.24-2.13 (m, 1H), 2.08-1.91 (m, 2H), 1.80-1.29 (m, 6H).

Source