Sodium Hydroxide → 3,4-Dihydro-1H-beta-carboline-2,9-dicarboxylic acid 2-tert-butyl ester 9-(2,2,2-trichloro-ethyl) ester

HRID 992414ノート

反応式

HRID 992414 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]([Cl:29])([Cl:28])[CH2:23][O:24][C:25](Cl)=[O:26].[OH-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Cl:21][C:22]([Cl:29])([Cl:28])[CH2:23][O:24][C:25]([N:11]1[C:10]2[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:20][CH2:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:26]

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 18377349tert-butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

生成物 1

HCID 698941943,4-Dihydro-1H-beta-carboline-2,9-dicarboxylic acid 2-tert-butyl ester 9-(2,2,2-trichloro-ethyl) ester収率 28%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

1,3,4,9-Tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester (7.68 g), 2,2,2-trichloroethylchloroformate (5.8 ml), sodium hydroxide (2.8 g) and tetrabutylammonium iodide (catalytic) in dichloromethane (100 ml) were stirred under nitrogen at room temperature for 5 h. The mixture was diluted with dichloromethane (100 ml), washed with water (150 ml) and brine (100 ml), then dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed (SiO2, 1% methanol in dichloromethane) to give the title compound (3.53 g, 28%) as a yellow foam.

後処理

  1. washwashed with water (150 ml) and brine (100 ml)
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. customThe residue was chromatographed (SiO2, 1% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-de1e37f8d1ba453f964b7a769b225baa
出典データセット
uspto-grants-2002_10
特許番号
US06469020B2

反応ノート

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