benzyl [(3R,7S)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate → (3R,7S)-3-amino-1-methyl-7-phenylazepan-2-one

HRID 1392079Notes

Reaction equation

HRID 1392079 reaction equation
[CH3:1][N:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH2:5][C@@H:4]([NH:15]C(=O)OCC2C=CC=CC=2)[C:3]1=[O:26]>[OH-].[OH-].[Pd+2].CCO>[NH2:15][C@@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:2]([CH3:1])[C:3]1=[O:26]

Participants

4

Reactant 1

HCID 58691193benzyl [(3R,7S)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate

Product 1

HCID 58691164(3R,7S)-3-amino-1-methyl-7-phenylazepan-2-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl [(3R,7S)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate (3c) (310 mg) and Pearlman's catalyst (62 mg) in EtOH (8 mL) was hydrogenated at 45 psi for 6 h. The reaction mixture was filtered through Celite and concentrated in vacuo. The residue was dissolved in DCM and washed with saturated NaHCO3, brine, dried (Na2SO4), filtered and concentrated to a viscous oil. The aqueous layer was extracted with DCM (3×). The combined organic layer was washed with brine, dried (Na2SO4), filtered and concentrated to a viscous oil. (166 mg, 86%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with saturated NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to a viscous oil
  8. extractionThe aqueous layer was extracted with DCM (3×)
  9. washThe combined organic layer was washed with brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated to a viscous oil

Sources & evidence

ORD record
ord-8c0ee51ecfb241d5abcf68ac63b392ce
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

Loading…