Hydrazine hydrate (1:1) → HCID 58691203、化合物

HRID 1392085ノート

反応式

HRID 1392085 の反応式
[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]

参加物

6

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 58691210HCID 58691210、化合物

生成物 2

HCID 58691195(7R)-3-amino-1-(cyclopropylmethyl)-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-oneHCID 58691203HCID 58691203、化合物収率 82%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-c71cd0531a524bbdb9c581f3cb833b83
出典データセット
uspto-grants-2008_03
特許番号
US07342007B2

反応ノート

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