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Ethyl bromoacetate → Ethyl (2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate

HRID 2236095
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HRID 2236095 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:20][CH2:19][C:11]2[NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:20][CH2:19][C:11]2[N:12]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 46344376tert-Butyl 1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

생성물 1

HCID 71063767Ethyl (2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate수율 70.4%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a stirred suspension of crude 2-tert.-butoxycarbonyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol (33.5 mmol) and caesium carbonate (25.1 g, 77.1 mmol) in dry acetone is added ethyl bromoacetate (5.6 ml, 50.3 mmol). The reaction mixture is stirred at rt overnight and then filtered over a small plug of Celite. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel column chromatography (hexane/EtOAc 5:1) to afford pure sub-title compound as yellow oil (8.45 g) in 70% yield (over two steps). tR (LC-2) 2.46 min; ESI-MS (positive ion): m/z 381.54 [M+Na]+ (calcd 358.43 for C20H26N2O4).

후처리

  1. filtrationfiltered over a small plug of Celite
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customthe residue is purified by silica gel column chromatography (hexane/EtOAc 5:1)

출처 및 근거

ORD 기록
ord-5e5eed469a0a4ba69de330b73d6eba4a
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07714132B2

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