4-benzyloxycarbonylamino-N-(4,4-difluorocyclohexyl)bicyclo[2.2.2]octane-1-carboxamide → 4-amino-N-(4,4-difluorocyclohexyl)bicyclo[2.2.2]octane-1-carboxamide

HRID 228036Notes

Reaction equation

HRID 228036 reaction equation
C(OC([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([NH:22][CH:23]3[CH2:28][CH2:27][C:26]([F:30])([F:29])[CH2:25][CH2:24]3)=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=O)C1C=CC=CC=1.[H][H]>O1CCCC1.[C].[Pd]>[NH2:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([NH:22][CH:23]3[CH2:28][CH2:27][C:26]([F:29])([F:30])[CH2:25][CH2:24]3)=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2

Participants

5

Reactant 2

HCID 231505664-benzyloxycarbonylamino-N-(4,4-difluorocyclohexyl)bicyclo[2.2.2]octane-1-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 231507184-amino-N-(4,4-difluorocyclohexyl)bicyclo[2.2.2]octane-1-carboxamideYield 101%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Benzyloxycarbonylamino-N-(4,4-difluorocyclohexyl)bicyclo[2.2.2]octane-1-carboxamide (55.4 mg) was dissolved in tetrahydrofuran (6 mL). To this solution, 10% palladium carbon (20.0 mg) was added and the mixture was stirred at room temperature for 6 hours in a hydrogen atmosphere. The reaction mixture was filtered to remove the catalyst and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column (eluant:ethyl acetate:methanol=10:1) to give 4-amino-N-(4,4-difluorocyclohexyl)bicyclo[2.2.2]octane-1-carboxamide (38.1 mg) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by a silica gel column (eluant:ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-a2c10124e97a477da46648bdd070ac3b
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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