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

HRID 1392094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392094
[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]

Komponenten

6

Edukt 2

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

Produkt 2

HCID 58691186HCID 58691186, VerbindungHCID 58691198HCID 58691198, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-919291e9b4284c4ea1ad97556b943bfa
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342007B2

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