Tert-butyl 3-pyridin-4-yl-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate → Tert-butyl 3-pyridin-4-yl-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 599352Notes

Reaction equation

HRID 599352 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH2:13][CH:12]3[N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:9]([CH2:10][CH2:11]3)[CH:8]=2)=[CH:3][CH:2]=1>CO.[Pd]>[N:1]1[CH:6]=[CH:5][C:4]([CH:7]2[CH2:8][CH:9]3[N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]([CH2:11][CH2:10]3)[CH2:13]2)=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 67268174Tert-butyl 3-pyridin-4-yl-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate

Product 1

HCID 67267778Tert-butyl 3-pyridin-4-yl-8-azabicyclo[3.2.1]octane-8-carboxylateYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a high-pressure reactor, under nitrogen, 0.17 g of 5% palladium-on-charcoal is added to 0.46 g of tert-butyl 3-pyridin-4-yl-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate solubilized in 20 ml of methanol. The reaction mixture is placed under a hydrogen pressure of 3 atmospheres at 25° C., and mechanically stirred for two and a half hours. The palladium is filtered off on Whatman paper and washed with methanol. The solvent is evaporated off and 0.46 g of tert-butyl 3-pyridin-4-yl-8-azabicyclo[3.2.1]octane-8-carboxylate is obtained.

Workup

  1. customat 25° C.
  2. filtrationThe palladium is filtered off on Whatman paper
  3. washwashed with methanol
  4. customThe solvent is evaporated off

Sources & evidence

ORD record
ord-8fe530fba61b45dbac5095d60b0426d3
Source dataset
uspto-grants-2011_03
Patent number
US07897773B2

Reaction notes

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