Reaction #1702049

Reaction equation

methyl 4-[(1R)-3-oxocyclopentyl]benzoate

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

→

title compound

Methyl 4-[(1R,3S)-3-[[(1R)-1-(4-fluoro-3-methoxy-phenyl)ethyl]-amino]cyclopentyl]benzoate

Conditions

Workup

1. 1
   OtherThe resulting isomers were separated by flash chromatography (gradient of 0-50% EtOAc in heptane containing 3% NEt3)
2. 2
   WashThe faster eluting peak
3. 3
   Otherwas isolated

Procedure

General procedure B was followed using methyl 4-[(1R)-3-oxocyclopentyl]benzoate (preparation 32) as the ketone and (1R)-1-(4-fluoro-3-methoxyphenyl)ethylamine hydrochloride as the amine. The resulting isomers were separated by flash chromatography (gradient of 0-50% EtOAc in heptane containing 3% NEt3). The faster eluting peak was isolated to afford the title compound. 1H NMR (300 MHz, DMSO) 7.86 (d, J=8.3 Hz, 2H), 7.38 (d, J=8.3 Hz, 2H), 7.15 (dd, J=8.7, 1.8 Hz, 1H), 7.09 (dd, J=11.5, 8.3 Hz, 1H), 6.91-6.85 (m, 1H), 3.83 (2s, 6H), 3.80-3.70 (m, 1H), 3.05-2.86 (m, 2H), 2.22-1.52 (m, 5H), 1.41-1.27 (m, 1H), 1.23 (d, J=6.6 Hz, 3H).

Source