4-Cyclohexyl-4-(2-methoxycarbonyl-vinyl)-piperidine-1-carboxylic acid tert-butyl ester → 4-Cyclohexyl-4-(2-methoxycarbonylethyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1795169Notes

Reaction equation

HRID 1795169 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)([CH:14]=[CH:15][C:16]([O:18][CH3:19])=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 695971104-Cyclohexyl-4-(2-methoxycarbonyl-vinyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 233886974-Cyclohexyl-4-(2-methoxycarbonylethyl)-piperidine-1-carboxylic acid tert-butyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-cyclohexyl-4-(2-methoxycarbonyl-vinyl)-piperidine-1-carboxylic acid tert-butyl ester, 8, (2.64 g, 7.5 mmole) in methanol (30 ml) is added 10% palladium on carbon (120 mg) under argon. The mixture is purged with hydrogen and then stirred for two hours under a hydrogen atmosphere at atmospheric pressure. The reaction mixture is filtered through a short pad of Celite and the filtrate concentrated under reduced pressure. The crude product is purified over silica to afford 2.57 g (97% yield) of the desired compound.

Workup

  1. customThe mixture is purged with hydrogen
  2. filtrationThe reaction mixture is filtered through a short pad of Celite
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe crude product is purified over silica

Sources & evidence

ORD record
ord-8f83c134885c4f5ab4d7d022b1ae5384
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

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