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

HRID 992414노트

반응식

HRID 992414 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-de1e37f8d1ba453f964b7a769b225baa
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06469020B2

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