Tert-butyl 4-(4-bromophenyl)-3,6-dihydropyridine-1(2h)-carboxylate → 1-N-Boc-4-(4-bromophenyl)piperidine

HRID 447311Notes

Reaction equation

HRID 447311 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.[H][H]>CCOC(C)=O.[Rh]>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:9][CH2:10]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 2

HCID 54371851Tert-butyl 4-(4-bromophenyl)-3,6-dihydropyridine-1(2h)-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 272817821-N-Boc-4-(4-bromophenyl)piperidineYield 546.6%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe mixture was filtered through a cake of Celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a69f9de184f94c7c8ebdbe5deaca66a8
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Reaction notes

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