t-Butyl 3-(4-fluorobenzylidene)-1-piperidinecarboxylate → tert-Butyl 3-(4-fluorobenzyl)piperidine-1-carboxylate

HRID 497448Notes

Reaction equation

HRID 497448 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH:6]=[C:7]2[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 69411688t-Butyl 3-(4-fluorobenzylidene)-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 12174826tert-Butyl 3-(4-fluorobenzyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirring solution of the t-Butyl 3-(4-fluorobenzylidene)-1-piperidinecarboxylate (3.82 g, 13.1 mmol) and 10% palladium on carbon (0.76 g) in degassed methanol (200 mL) was added hydrogen gas to 55 psi. The reaction was stirred for 16 h and then filtered through a pad of celite. The celite was washed with methanol (200 mL). The filtrates were combined and concentration in vacuo to yield 2.76 g as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.12-7.07 (m, 2H), 6.98-6.93 (m, 2H), 3.89 (dt, J=13, J′=4, 1H), 3.84-3.74 (m, 1H), 2.57-2.43 (m, 4H), 1.75-1.60 (m, 4H), 1.42 (s, 9H), 1.15-1.09 (m, 1H).

Workup

  1. filtrationfiltered through a pad of celite
  2. washThe celite was washed with methanol (200 mL)
  3. concentrationconcentration in vacuo
  4. customto yield 2.76 g as a colorless oil

Sources & evidence

ORD record
ord-83faae855712478bb428f71c4da69c0d
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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