Реакция #1702054

ord-a699f3952ca14a8d84f230122f3753a4

Уравнение реакции

O=C1CC[C@@H](c2ccc(Br)cc2)C1
(3R)-3-(4-Bromo-phenyl)-cyclopentanone
COc1cc([C@@H](C)N)ccc1F.Cl
(1R)-1-(4-fluoro-3-methoxyphenyl)ethylamine hydrochloride
COc1cc([C@@H](C)N[C@H]2CC[C@@H](c3ccc(Br)cc3)C2)ccc1F
title compound
COc1cc([C@@H](C)N[C@H]2CC[C@@H](c3ccc(Br)cc3)C2)ccc1F
[(1S,3R)-3-(4-Bromo-phenyl)-cyclopentyl]-(1R)-[1-(4-fluoro-3-methoxy-phenyl)-ethyl]-amine

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

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

Методика

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).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08765676B2uspto-grants-2014_07