tert-butyl 4-pyridin-4-yl-3,6-dihydro-2H-pyridine-1-carboxylate → Tert-butyl 4-(pyridin-4-yl)piperidine-1-carboxylate

HRID 551795Notes

Reaction equation

HRID 551795 reaction equation
[N:1]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[N:10]1[CH:11]=[CH:12][C:7]([CH:4]2[CH2:5][CH2:6][N:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:2][CH2:3]2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 67191026tert-butyl 4-pyridin-4-yl-3,6-dihydro-2H-pyridine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 22061398Tert-butyl 4-(pyridin-4-yl)piperidine-1-carboxylateYield 66.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.336 g of 5% Pd/C is added to 0.821 g of tert-butyl 3,6-dihydro-4,4′-bipyridine-1(2H)-carboxylate, dissolved in 65 ml of methanol, in a high-pressure reactor under nitrogen. The reaction mixture is placed under a pressure of 3 atmospheres of hydrogen at 25° C. and stirred mechanically for 1 h. The palladium is filtered off on Whatman paper (registered trademark) and is washed with methanol. The solvent is evaporated and the residue is then chromatographed on silica gel, heptane/ethyl acetate (8/2) to heptane/ethyl acetate (1/1) elution gradient. 0.552 g of tert-butyl 4-(pyridin-4-yl)piperidine-1-carboxylate is obtained.

Workup

  1. filtrationThe palladium is filtered off on Whatman paper (registered trademark)
  2. washis washed with methanol
  3. customThe solvent is evaporated
  4. customthe residue is then chromatographed on silica gel, heptane/ethyl acetate (8/2) to heptane/ethyl acetate (1/1) elution gradient

Sources & evidence

ORD record
ord-53bc66ee306a4eb09e673145b19a51d5
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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