Sodium Hydroxide → (2'S,3R,4'E,6'S)-6-bromo-2'-(3-chlorophenyl)-4'-hydroxyimino-6'-methoxyspiro[1H-indole-3,1'-cyclohexane]-2-one

HRID 1987800ノート

反応式

HRID 1987800 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH:16]([O:17][CH3:18])[CH2:15][C:14](=O)[CH2:13][CH:12]3[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[OH-:27].[NH4+:28].Cl.[OH-].[Na+]>CCO>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C@:6]3([C@@H:16]([O:17][CH3:18])[CH2:15]/[C:14](=[N:28]/[OH:27])/[CH2:13][C@H:12]3[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 13908798HCID 13908798、化合物HCID 68903423Rac-(1r,2s,6s)-6'-bromo-2-(3-chlorophenyl)-6-methoxyspiro[cyclohexane-1,3'-[3h]indole]-2',4(1'h)-dione

生成物 1

HCID 57724966(2'S,3R,4'E,6'S)-6-bromo-2'-(3-chlorophenyl)-4'-hydroxyimino-6'-methoxyspiro[1H-indole-3,1'-cyclohexane]-2-one収率 46%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To the suspension of rac-(1R,2S,6S)-6′-bromo-2-(3-chlorophenyl)-6-methoxyspiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione (1.69 g, 3.89 mmol) and NH4OH—HCl (0.27 g, 3.89 mmol) in EtOH (40 mL) was added a queous NaOH solution (1N, 4 mL, 4 mmol). The reaction mixture was heated at 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=1:3, 1:2, then 1:1) to give the less polar product rac-E-(1R,2S,6S)-6′-bromo-2-(3-chlorophenyl)-6-methoxy spiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione-4-oxime as a white solid (0.8 g, 46%): HRMS (ES+) m/z Calcd for C22H18BrClN2O3+H [(M+H)+]: 449.0262, Found: 449.0260; rac-Z-(1R,2S,6S)-6′-bromo-2-(3-chlorophenyl)-6-methoxy spiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione-4-oxime as a white solid (0.8 g, 46%): HRMS (ES+) m/z Calcd for C22H18BrClN2O3+H [(M+H)+]: 449.0262, Found: 449.0261.

後処理

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

出典と根拠

ORDレコード
ord-5d881a2198594b03a08f4dcc0b645fcb
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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