Hydrazine hydrate (1:1) → HCID 58691198, compound

HRID 1392094Notes

Reaction equation

HRID 1392094 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[CH:9][CH2:8][CH:7]([N:18]2C(=O)C3C(=CC=CC=3)C2=O)[C:6]1=[O:29].O.NN>CO.CCOCC>[NH2:18][C@@H:7]1[CH2:8][CH:9]=[CH:10][C@@H:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:6]1=[O:29].[NH2:18][C@H:7]1[CH2:8][CH:9]=[CH:10][C@@H:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:6]1=[O:29]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58691182HCID 58691182, compound

Product 2

HCID 58691186HCID 58691186, compoundHCID 58691198HCID 58691198, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To 2-[(7S)-1-(2-methoxyethyl)-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]-1H-isoindole-1,3(2H)-dione (6c) (420 mg) dissolved in MeOH (10 mL) was added hydrazine hydrate (0.1 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 in 1:1 ether/DCM) to give (3R,7S)-3-amino-1-(2-methoxyethyl)-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-one (6e) and (3S,7S)-3-amino-1-(2-methoxyethyl)-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-one (6d) (combined yield of 67%).

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 in 1:1 ether/DCM)

Sources & evidence

ORD record
ord-919291e9b4284c4ea1ad97556b943bfa
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

Loading…