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Water → HCID 86755052, 화합물

HRID 849601
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HRID 849601 반응식
[CH3:1][O:2][C:3]([C:5]12[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH:11]=[C:10](I)[CH:9]1[CH2:8][N:7]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:6]2)=[O:4].C(=O)([O-])[O-].[Na+].[Na+].O.C(O[CH2:39][CH3:40])(=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]12[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH:11]=[C:10]([C:40]3[CH:39]=[CH:8][C:9]4[C:5](=[CH:13][CH:12]=[CH:11][CH:10]=4)[CH:3]=3)[CH:9]1[CH2:8][N:7]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:6]2)=[O:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 86755053HCID 86755053, 화합물

생성물 1

HCID 86755052HCID 86755052, 화합물수율 67%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

240 mg of tetrakis(triphenylphosphine)palladium and then a solution of 0.69 g of 2-naphthylboronic acid, isolated in the trimer anhydride form, in 20 cm3 of methanol were added to a solution of 2 g of methyl(3aRS,4SR,7aRS)-2-benzyl-7-iodo-4-phenyl-2,3,3a,4,5,7a-hexahydro-1H-isoindole-3a-carboxylate in 40 cm3 of toluene. 45 cm3 of a 2N aqueous sodium carbonate solution were added dropwise and the reaction mixture is brought to reflux for four hours. After cooling, 80 cm3 of water and 60 cm3 of ethyl acetate were added. The organic phase was separated by settling, washing with water to neutrality and dried over magnesium sulphate. After concentrating the solvent under reduced pressure, the residue was purified by flash chromatography on silica gel (230-400 mesh), elution being carried out with a mixture of cyclohexane and of ethyl acetate (90/10 by volume). 1.33 g (67%) of methyl(3aRS,4SR,7aRS)-2-benzyl-7-(2-naphthyl)-4-phenyl-2,3,3a,4,5,7a-hexahydro-1H-isoindole-3a-carboxylate were thus obtained in the form of a white foam, the characteristic of which was as follows:

후처리

  1. temperatureto reflux for four hours
  2. temperatureAfter cooling
  3. customThe organic phase was separated
  4. washwashing with water to neutrality
  5. dry with materialdried over magnesium sulphate
  6. concentrationAfter concentrating the solvent under reduced pressure
  7. customthe residue was purified by flash chromatography on silica gel (230-400 mesh), elution
  8. additionbeing carried out with a mixture of cyclohexane and of ethyl acetate (90/10 by volume)

출처 및 근거

ORD 기록
ord-e0d8f1a55d13450585d3af49310eb3a4
출처 데이터셋
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06013662

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