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

HRID 1614872Notes

Reaction equation

HRID 1614872 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][C:10](=O)[CH2:9]2)=[CH:4][CH:3]=1.Cl.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C@H:22]([NH2:24])[CH3:23])=[CH:18][C:17]=1[O:25][CH3:26]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][C@H:10]([NH:24][C@@H:22]([C:19]3[CH:20]=[CH:21][C:16]([F:15])=[C:17]([O:25][CH3:26])[CH:18]=3)[CH3:23])[CH2:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 49833221(R)-3-(4-Bromophenyl)cyclopentan-1-oneHCID 53484667(R)-1-(4-Fluoro-3-methoxyphenyl)ethanamine hydrochloride

Product 1

HCID 68749655[(1S,3R)-3-(4-Bromo-phenyl)-cyclopentyl]-(1R)-[1-(4-fluoro-3-methoxy-phenyl)-ethyl]-amine

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).

Workup

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

Sources & evidence

ORD record
ord-a699f3952ca14a8d84f230122f3753a4
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

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