1-t-butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]-3,6-dihydro-2H-pyridine → 1-t-Butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]piperidine

HRID 497337Notes

Reaction equation

HRID 497337 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([CH:14]([C:22]([OH:24])=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH:14]([C:22]([OH:24])=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 223186591-t-butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]-3,6-dihydro-2H-pyridine

Product 1

HCID 223186671-t-Butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]piperidineYield 71.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

5.0 g of 1-t-Butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]-3,6-dihydro-2H-pyridine was dissolved in 50 ml of methanol, and 0.50 g of palladium hydroxide/carbon was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 days. After removal of the catalyst by Celite filtration, the filtrate was concentrated under reduced pressure to give 3.6 g of a crude 1-t-butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]piperidine.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby Celite filtration
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-490b9368f2424dfbacb0659c2b2eb429
Source dataset
uspto-grants-2005_09
Patent number
US06949552B2

Reaction notes

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