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

HRID 1392075Notes

Reaction equation

HRID 1392075 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 58691158benzyl [(3S,7S)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate

Product 1

HCID 9990953(3S,7S)-3-amino-1-methyl-7-phenylazepan-2-oneYield 90%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl [(3S,7S)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate (2c) (216 mg) and Pearlman's catalyst (40 mg) in EtOH (7 mL) was hydrogenated at 45 psi overnight. The reaction mixture was filtered through Celite and concentrated in vacuo. The residue was dissolved in EtOAc and washed with saturated NaHCO3, brine, dried (Na2SO4), filtered and concentrated to a viscous oil. The aqueous layer from above were extracted 3×50 ml DCM. The combined organic layer was washed with brine, dried (Na2SO4), filtered and concentrated to a viscous oil (60 mg). The two isolated oils were combined to give a 90% yield of the desired product. 1H NMR (300 MHz, CDCl3) δ 1.57-2.12 (m, 9H), 2.53 (s, 3H), 4.92 (d, 1H), 7.26-7.41 (m, 5H). APCI, m/z=219 (M+1). LC/MS 1.82 min., Method A

Workup

  1. customwas hydrogenated at 45 psi overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with saturated NaHCO3, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a viscous oil
  9. extractionThe aqueous layer from above were extracted 3×50 ml DCM
  10. washThe combined organic layer was washed with brine
  11. dry with materialdried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated to a viscous oil (60 mg)

Sources & evidence

ORD record
ord-a63b3c0543724793a06902dbf882229f
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

Loading…