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

HRID 1392094노트

반응식

HRID 1392094 반응식
[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]

참가 물질

6

반응물 2

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

생성물 2

HCID 58691186HCID 58691186, 화합물HCID 58691198HCID 58691198, 화합물수율 67%

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-919291e9b4284c4ea1ad97556b943bfa
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342007B2

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