Hydrazine hydrate (1:1) → HCID 58691203, compound

HRID 1392085Notes

Reaction equation

HRID 1392085 reaction equation
[CH:1]1([CH2:4][N:5]2[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=[CH:9][CH2:8][CH:7]([N:18]3C(=O)C4C(=CC=CC=4)C3=O)[C:6]2=[O:29])[CH2:3][CH2:2]1.O.NN>CO.CCOCC>[NH2:18][CH:7]1[CH2:8][CH:9]=[CH:10][C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[C:6]1=[O:29].[NH2:18][CH:7]1[CH2:8][CH:9]=[CH:10][C@@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[C:6]1=[O:29]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58691210HCID 58691210, compound

Product 2

HCID 58691195(7R)-3-amino-1-(cyclopropylmethyl)-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-oneHCID 58691203HCID 58691203, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To 2-[1-(cyclopropylmethyl)-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]-1H-isoindole-1,3(2H)-dione (4d) (126 mg) dissolved in MeOH (4 mL) was added hydrazine hydrate (0.033 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 to an oil. The diastereomeric mixture was separated via preparative plate chromatography (eluent 10% MeOH/DCM) to give (7R)-3-amino-1-(cyclopropylmethyl)-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-one (4f) (28 mg) and (7S)-3-amino-1-(cyclopropylmethyl)-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-one (4e) (40 mg) (combined yield of 82%).

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 to an oil
  9. customThe diastereomeric mixture was separated via preparative plate chromatography (eluent 10% MeOH/DCM)

Sources & evidence

ORD record
ord-c71cd0531a524bbdb9c581f3cb833b83
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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