Methanol → racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-1'-[(hydroxycarbonyl)-methyl]-2'-(2-methylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1727994ノート

反応式

HRID 1727994 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:36])[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])[N:12]([CH2:24][C:25]([O:27]C)=[O:26])[CH:11]3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[C:5]2=[CH:4][CH:3]=1.CO.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:36])[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])[N:12]([CH2:24][C:25]([OH:27])=[O:26])[CH:11]3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[C:5]2=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 131727320racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-1'-[(methoxycarbonyl)-methyl]-2'-(2-methylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

生成物 1

HCID 73315581racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-1'-[(hydroxycarbonyl)-methyl]-2'-(2-methylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To the solution of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-1′-[(methoxycarbonyl)-methyl]-2′-(2-methylphenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.21 g, 0.4 mmol) prepared in 29b in the mixture of methanol (10 mL) and tetrahydrofuran (20 mL) was added aqueous NaOH solution (1N, 10 mL, 10 mmol). The reaction mixture was stirred at room temperature for overnight and then concentrated. The residue was neutralized to “pH” ˜7, then extracted with ethyl acetate. The organic layer was separated, washed with H2O, brine, dried over MgSO4 and concentrated to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-1′-[(hydroxycarbonyl)-methyl]-2′-(2-methylphenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white foam.

後処理

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with H2O, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-7bcdc78ee2964eceb69bed4f5ad49a1a
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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