HCID 13908798、化合物 → (2'S,3S,4'Z,6'S)-6-bromo-2'-(3-chlorophenyl)-4'-hydroxyimino-6'-prop-1-en-2-ylspiro[1H-indole-3,1'-cyclohexane]-2-one

HRID 1987801ノート

反応式

HRID 1987801 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH:16]([C:17]([CH3:19])=[CH2:18])[CH2:15][C:14](=O)[CH2:13][CH:12]3[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[OH-:28].[NH4+:29].Cl>CCO.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C@@:6]3([C@H:16]([C:17]([CH3:19])=[CH2:18])[CH2:15]/[C:14](=[N:29]/[OH:28])/[CH2:13][C@H:12]3[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 13908798HCID 13908798、化合物HCID 68904372rac-(1S,2S,6R)-6'-bromo-2-(3-chlorophenyl)-6-isopropenyl spiro[cyclohexane-1,3'-[3H]indole]-2',4(1'H)-dione

生成物 1

HCID 140531877(2'S,3S,4'Z,6'S)-6-bromo-2'-(3-chlorophenyl)-4'-hydroxyimino-6'-prop-1-en-2-ylspiro[1H-indole-3,1'-cyclohexane]-2-one収率 75.3%

試薬・触媒・溶媒 1

HCID 19096565Water ethanol溶媒

実験手順

The suspension of rac-(1S,2S,6R)-6′-bromo-2-(3-chlorophenyl)-6-isopropenyl spiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione (0.23 g, 0.52 mmol) and NH4OH—HCl (0.1 g, 0.52 mmol) in EtOH-water (3/2, 20 mL) was allowed to reflux for 1 h. TLC analysis indicated the formation of desired product and complete consumption of starting material. The reaction was cooled to room temperature, and water was added. The mixture was extracted with ethyl acetate. The organic layer was separated, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:2, then 1:1) to give the title compound as a white solid (0.18 g, 75%): HRMS (ES+) m/z Calcd for C22H20BrClN2O2+H [(M+H)+]: 459.0470, Found: 459.0470.

後処理

  1. temperatureto reflux for 1 h
  2. customthe formation of desired product and complete consumption of starting material
  3. additionwater was added
  4. extractionThe mixture was extracted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (EtOAc

出典と根拠

ORDレコード
ord-e626ec31474d466fb7e6a5543b68a760
出典データセット
uspto-grants-2009_06
特許番号
US07553833B2

反応ノート

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