Reaktion #534493

Reaktionsgleichung

tert-butyl 4-(4-bromophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

hydrogen

→

title compound

tert-Butyl-4-(4-bromophenyl)piperidine-1-carboxylate

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction mixture
2. 2
   FiltrationThe mixture was filtered through a cake of Celite
3. 3
   Einengenthe filtrate was concentrated

Vorschrift

To a solution of tert-butyl 4-(4-bromophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (100 mg, 0.30 mmol) in EtOAc was added Rh/C (8 mg, 0.03 mmol). The resulting reaction mixture was stirred at rt in a hydrogen atmosphere for 17 h. The mixture was filtered through a cake of Celite and the filtrate was concentrated to give the title compound as a colourless oil (558 mg, 94%). 1H NMR (400 MHz, CDCl3) δ 7.43 (d, J=8.4 Hz, 2H), 7.08 (d, J=8.3 Hz, 2H), 4.27-4.23 (m, 2H), 2.79 (t, J=12.9 Hz, 2H), 2.65-2.58 (m, 1H), 1.82-1.79 (m, 2H), 1.64-1.56 (m, 2H), 1.49 (s, 9H); MS ESI 361.9 [M+Na]+, calcd for [C16H22BrNO2+Na]+ 362.07.

Quelle