Ammonium Chloride → 6-chloro-4'-(3-chlorophenyl)-2'-(1-ethyl-1-hydroxy-propyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728049ノート

反応式

HRID 1728049 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:28])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24](=[O:27])[CH2:25][CH3:26])[C:5]2=[CH:4][CH:3]=1.[CH2:29]([Mg]Cl)[CH3:30].[NH4+].[Cl-]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:28])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24]([CH2:29][CH3:30])([OH:27])[CH2:25][CH3:26])[C:5]2=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 76568170HCID 76568170、化合物HCID 178461633HCID 178461633、化合物

生成物 1

HCID 765680146-chloro-4'-(3-chlorophenyl)-2'-(1-ethyl-1-hydroxy-propyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione収率 93.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-propionylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (100 mg, 0.24 mmol) prepared in example 103 in tetrahydrofuran (3 mL) at −78° C. was added a tetrahydrofuran solution of ethylmagnesium chloride (2M, 6 mL, 12 mmol). The reaction mixture was stirred at −78° C. for 0.5 h, then slowly warmed to room temperature and stirred for 2 h. The mixture was poured into saturated aqueous NH4Cl solution, and the mixture was extracted with ethyl acetate. The organic layer was separated, dried over MgSO4, concentrated. The residue was purified by chromatography (EtOAc:MeOH=10:1) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(1-ethyl-1-hydroxy-propyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 100 mg, 93%)

後処理

  1. temperatureslowly warmed to room temperature
  2. stirringstirred for 2 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (EtOAc:MeOH=10:1)

出典と根拠

ORDレコード
ord-d8e6517fa2334e66b5ff9259661aa145
出典データセット
uspto-grants-2009_02
特許番号
US07495007B2

反応ノート

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