Ethyl 4-(benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate → Ethyl 4-aminobicyclo[2.2.2]octane-1-carboxylate

HRID 555675

Reaction equation

HRID 555675 reaction equation
C(OC([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=O)C1C=CC=CC=1.[H][H]>C(O)C.[C].[Pd]>[NH2:11][C:12]12[CH2:17][CH2:16][C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])([CH2:14][CH2:13]1)[CH2:18][CH2:19]2

Participants

5

Reactant 2

HCID 10616503Ethyl 4-(benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 23149693Ethyl 4-aminobicyclo[2.2.2]octane-1-carboxylateYield 100.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Ethyl 4-benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxylate (40.0 g) was dissolved in ethanol (400 mL). To this solution, 10% palladium-carbon (4.00 g) was added and the mixture was stirred at room temperature for 6 hours in a stream of hydrogen. The catalyst in the reaction mixture was filtered through a Celite pad and the filtered catalyst, together with the Celite pad, was washed with ethanol. The filtrate and the washings were combined and concentrated under reduced pressure. The resulting residue was dried under reduced pressure to give ethyl 4-aminobicyclo[2.2.2]octane-1-carboxylate (23.9 g).

Workup

  1. filtrationThe catalyst in the reaction mixture was filtered through a Celite pad
  2. washthe filtered catalyst, together with the Celite pad, was washed with ethanol
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was dried under reduced pressure

Sources & evidence

ORD record
ord-2b82e76f8a234554b2fedbe45a240614
Source dataset
uspto-grants-2011_11
Patent number
US08053465B2

Linked notes

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