4-(5-Fluoro-2-methoxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester → 4-(5-Fluoro-2-methoxyphenyl)piperidine-1-carboxylic acid t-butyl ester

HRID 32264Notes

Reaction equation

HRID 32264 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 597694194-(5-Fluoro-2-methoxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester

Product 1

HCID 597693774-(5-Fluoro-2-methoxyphenyl)piperidine-1-carboxylic acid t-butyl esterYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(5-fluoro-2-methoxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (2.0 g, 6.5 mmol) produced in Example (106a) in methanol (30 mL) was added 10% palladium on carbon (0.99 g, wet), the mixture was stirred for 17 hours at atmospheric pressure and room temperature under a hydrogen atmosphere. The reaction mixture was filtered through Celite, and the obtained filtrate was concentrated under reduced pressure to give 2.0 g of the title compound as a light yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe obtained filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d65c4429084d4e2bb21842c6b61a5e55
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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