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Cesium carbonate → Ethyl (3S)-3-[4-[[4-(spiro[indane-1,4'-piperidine]-1'-ylmethyl)phenyl]methoxy]phenyl]hex-4-ynoate

HRID 390403
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HRID 390403 반응식
[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:21]([O:23][C:24](=[O:46])[CH2:25][CH:26]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([CH2:44]Br)=[CH:40][CH:39]=2)=[CH:32][CH:31]=1)[C:27]#[C:28][CH3:29])[CH3:22]>C(#N)C>[N:1]1([CH2:44][C:41]2[CH:40]=[CH:39][C:38]([CH2:37][O:36][C:33]3[CH:34]=[CH:35][C:30]([C@@H:26]([C:27]#[C:28][CH3:29])[CH2:25][C:24]([O:23][CH2:21][CH3:22])=[O:46])=[CH:31][CH:32]=3)=[CH:43][CH:42]=2)[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 156376162,3-Dihydrospiro(indene-1,4'-piperidine)HCID 670873073-[4-(4-Bromomethyl-benzyloxy)-phenyl]-hex-4-ynoic acid ethyl ester

생성물 1

HCID 58230573Ethyl (3S)-3-[4-[[4-(spiro[indane-1,4'-piperidine]-1'-ylmethyl)phenyl]methoxy]phenyl]hex-4-ynoate수율 93.7%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

To a solution of 2,3-dihydrospiro[indene-1,4′-piperidine] (0.37 g, 1.68 mmol) in acetonitrile (20.0 mL), is added Cs2CO3 (1.37 g, 4.21 mmol at room temperature, followed by the addition of 3-[4-(4-bromomethyl-benzyloxy)-phenyl]-hex-4-ynoic acid ethyl ester (0.70 g, 1.68 mmol). The reaction mixture is stirred overnight at room temperature. The reaction mixture is filtered through diatomaceous earth and the filtrate is evaporated. The crude product is purified by silica gel column chromatography (gradient 3% methanol in DCM) to give the title compound as colorless gel, (0.82 g, 93.7%). ESI/MS 522.2 (M+H)+.

후처리

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. customthe filtrate is evaporated
  3. customThe crude product is purified by silica gel column chromatography (gradient 3% methanol in DCM)

출처 및 근거

ORD 기록
ord-aaddc74571b04fd2972abedbeb097ddd
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08383642B2

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