N-t-butoxycarbonyl-4-(4-fluorobenzylidene)piperidine → 4-(4-Fluoro-benzyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1006373Notes

Reaction equation

HRID 1006373 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][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.[C].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][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])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 22676694N-t-butoxycarbonyl-4-(4-fluorobenzylidene)piperidine

Product 1

HCID 226766794-(4-Fluoro-benzyl)-piperidine-1-carboxylic acid tert-butyl esterYield 84.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

1-tert-Butoxycarbonyl-4-(4-fluorobenzylidene)piperidine (47.0 g) was dissolved in methanol (450 ml). 10% Palladium carbon (containing 50% water, 4.7 g) was added to the solution and the mixture was subjected to catalytic hydrogenation for 5 hours. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give 1-tert-butoxycarbonyl-4-(4-fluorobenzyl)piperidine (39.9 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-539468d7fff0413c91ee5758abe89eff
Source dataset
uspto-grants-2004_09
Patent number
US06787650B1

Reaction notes

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