(6R,7aS)-6-Azido-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one → (6R,7aS)-6-Amino-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one

HRID 455257Notes

Reaction equation

HRID 455257 reaction equation
[N:1]([C@H:4]1[CH2:23][N:7]2[C:8](=[O:22])[N:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=3)[CH2:10][C@@H:6]2[CH2:5]1)=[N+]=[N-]>C1COCC1.[Pd]>[NH2:1][C@H:4]1[CH2:23][N:7]2[C:8](=[O:22])[N:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:19])[F:20])=[CH:13][CH:12]=3)[CH2:10][C@@H:6]2[CH2:5]1

Participants

4

Reactant 1

HCID 70975874(6R,7aS)-6-Azido-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one

Product 1

HCID 70976166(6R,7aS)-6-Amino-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-oneYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10% Pd/C (20 mg, 20%) was added to a solution of (6R,7aS)-6-Azido-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (100 mg, 0.3 mmol) in THF (10 mL), the mixture stirred for 30 minutes under H2. The mixture was filtered and concentrated. The residue was purified by silica gel column chromatography (dichloromethane/methnol=20:1) to give 80 mg (87%) of the title compound. LC-MS: 302.1 [M+1]+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography (dichloromethane/methnol=20:1)

Sources & evidence

ORD record
ord-4ee5be54cb264cb6b46bf8cfa0dc0d14
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

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