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

HRID 1392085노트

반응식

HRID 1392085 반응식
[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]

참가 물질

6

반응물 2

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

생성물 2

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

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%).

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

출처 및 근거

ORD 기록
ord-c71cd0531a524bbdb9c581f3cb833b83
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342007B2

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