Methyl 4-[(1-Boc-piperidin-4-ylidene)methyl]benzoate → 1-Piperidinecarboxylic acid, 4-[[4-(methoxycarbonyl)phenyl]methyl]-, 1,1-dimethylethyl ester

HRID 1006381Notes

Reaction equation

HRID 1006381 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:24]=[CH:23][C:8]([CH:9]=[C:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:7][CH:6]=1)=[O:4]>CO.[C].[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:14][CH2:15]2)=[CH:23][CH:24]=1)=[O:4]

Participants

4

Reactant 1

HCID 10616499Methyl 4-[(1-Boc-piperidin-4-ylidene)methyl]benzoate

Product 1

HCID 115373021-Piperidinecarboxylic acid, 4-[[4-(methoxycarbonyl)phenyl]methyl]-, 1,1-dimethylethyl esterYield 101.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-(4-methoxycarbonylbenzylidene)piperidine-1-carboxylate (6 g, 18 mmol) in methanol (150 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium-carbon (containing 50% water, 1 g) at room temperature for 5 hours. The catalyst was filtered off, and the filtrate was condensed under reduced pressure. The residue was purified by flash column chromatography (silica gel 90 g, ethyl acetate/hexane=1/10) to give the title compound as a pale yellow oil (6.1 g, 100%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customcondensed under reduced pressure
  3. customThe residue was purified by flash column chromatography (silica gel 90 g, ethyl acetate/hexane=1/10)

Sources & evidence

ORD record
ord-341b63f0f5384919aa4c6b6a98fbdc19
Source dataset
uspto-grants-2004_09
Patent number
US06787650B1

Reaction notes

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