tert-butyl 4-[3-(ethoxycarbonyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-[3-(ethoxycarbonyl)phenyl]piperidine-1-carboxylate

HRID 643534Notes

Reaction equation

HRID 643534 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 57880536tert-butyl 4-[3-(ethoxycarbonyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 57880576Tert-butyl 4-[3-(ethoxycarbonyl)phenyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 4-[3-(ethoxycarbonyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate (6.48 g, 19.6 mmol) and Pd(OH)2/C (20% Pd, lg) in 50 mL of methanol was stirred under a hydrogen atmosphere (balloon) for 18 h. The reaction mixture was then filtered through a celite plug, and the filtrate was concentrated to give tert-butyl 4-[3-(ethoxycarbonyl)phenyl]piperidine-1-carboxylate which did not require further purification. 1HNMR (CDCl3, 500 MHz): δ 7.91 (m, 2H), 7.40 (m, 2H), 4.40 (q, J=7.0 Hz, 2H), 4.28 (br s, 2H), 2.83 (m, 2H), 2.73 (tt, J=12.5, 4.0 Hz, 1H), 1.85 (br d, J=13.0 Hz), 1.67 dq, J=4.0, 12.5 Hz, 2H), 1.51 (s, 9H), 1.42 (t, J=7.0 Hz).

Workup

  1. filtrationThe reaction mixture was then filtered through a celite plug
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-42833ba87b814b29857a2c07bf6ad963
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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