Hydrazine hydrate (1:1) → HCID 58691198、化合物

HRID 1392094ノート

反応式

HRID 1392094 の反応式
[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]

参加物

6

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 58691182HCID 58691182、化合物

生成物 2

HCID 58691186HCID 58691186、化合物HCID 58691198HCID 58691198、化合物収率 67%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒

実験手順

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%).

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
  9. customThe diastereomeric mixture was separated via preparative plate chromatography (eluent 10% MeOH in 1:1 ether/DCM)

出典と根拠

ORDレコード
ord-919291e9b4284c4ea1ad97556b943bfa
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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