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Triphenylphosphine → 2-[2-((S)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl]-isoindole-1,3-dione

HRID 496417
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HRID 496417 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[CH2:13][N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24].[N:25]1([CH2:30][CH:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)O)[CH:29]=[CH:28][N:27]=[CH:26]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.CO.C(Cl)Cl>[N:25]1([CH2:30][C@H:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:1][C:2]2[CH:11]=[CH:10][C:9]3[C:8](=[O:12])[CH2:7][CH2:6][CH2:5][C:4]=3[C:3]=2[CH2:13][N:14]2[C:15](=[O:24])[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]2=[O:23])[CH:29]=[CH:28][N:27]=[CH:26]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 322392-(1H-imidazol-1-yl)-1-phenylethanolHCID 5462977Diethyl azodicarboxylateHCID 223248652-(2-Hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl)-isoindole-1,3-dione

생성물 1

HCID 600299192-[2-((S)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl]-isoindole-1,3-dione수율 87.7%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21226129Dichloromethane methanol용매

실험 절차

To a slurry of 2-(2-Hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl)-isoindole-1,3-dione (862 mg, 2.68 mmol) in THF (17 mL) was added ®-2-imidazol-1-yl-1-phenyl-ethanol (606 mg, 3.22 mmol) and triphenylphospine (846 mg, 3.22 mmol). After 15 min, diethylazodicarboxylate (0.51 mL, 3.22 mmol) was added and the reaction became homogenous. The reaction was stirred for 2 days and concentrated to give a reddish-brown foam. Purification by chromatography (10-20% acetone/CH2Cl2 then 5% MeOH/CH2Cl2) afforded the title compound as a light brown foam (1.15 g, 2.35 mmol, 87%). The structure was confirmed by NMR and mass spectrometry. MS m/z 492 (M++H).

후처리

  1. concentrationconcentrated
  2. customto give a reddish-brown foam
  3. customPurification by chromatography (10-20% acetone/CH2Cl2

출처 및 근거

ORD 기록
ord-9471ddd56bcd4969b2b044abea5c792a
출처 데이터셋
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06943183B2

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