Hydrazine hydrate (1:1) → (3S,7S)-3-amino-1-benzyl-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-one

HRID 1392090Notes

Reaction equation

HRID 1392090 reaction equation
[CH2:1]([N:8]1[C@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH2:11][CH:10]([N:21]2C(=O)C3C(=CC=CC=3)C2=O)[C:9]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CO.CCOCC>[NH2:21][C@@H:10]1[CH2:11][CH:12]=[CH:13][C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]1=[O:32].[NH2:21][C@H:10]1[CH2:11][CH:12]=[CH:13][C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]1=[O:32]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 586912052-[(7S)-1-benzyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]-1H-isoindole-1,3(2H)-dione

Product 2

HCID 58691160(3R,7S)-3-amino-1-benzyl-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-oneHCID 58691185(3S,7S)-3-amino-1-benzyl-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-oneYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To 2-[(7S)-1-benzyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]-1H-isoindole-1,3(2H)-dione (5c) (126 mg) dissolved in MeOH (4 mL) was added hydrazine hydrate (0.036 mL) and the mixture was stirred overnight at RT. A white precipitate formed in solution. The reaction mixture was diluted with ether and the precipitate was filtered and washed with ether. The etheral filtrate was concentrated and the resulting residue dissolved in DCM. The DCM solution was washed with H2O and brine, dried (Na2SO4) and concentrated. The diastereomeric mixture was separated via preparative plate chromatography (eluent 10% MeOH/DCM) to give (3R,7S)-3-amino-1-benzyl-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-one (5e) and (3S,7S)-3-amino-1-benzyl-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-one (5d) (combined yield of 72%).

Workup

  1. customA white precipitate formed in solution
  2. filtrationthe precipitate was filtered
  3. washwashed with ether
  4. concentrationThe etheral filtrate was concentrated
  5. dissolutionthe resulting residue dissolved in DCM
  6. washThe DCM solution was washed with H2O and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe diastereomeric mixture was separated via preparative plate chromatography (eluent 10% MeOH/DCM)

Sources & evidence

ORD record
ord-0b2d68dda2f5483a9c9e8ea502e9feda
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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