Phenol → (+/-)cis-1-(2-Benzylphenoxy)-2-tert-butoxycarbonylaminoindane

HRID 965218

反応式

HRID 965218 の反応式
[C:1]([O:5][C:6]([N:8]1[CH:10]2[CH2:11][C:12]3[C:17]([CH:9]12)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[C:30]([OH:31])=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:20][CH:19]=1.C1(O)C=CC=CC=1.C(OCC)C>C(Cl)(Cl)Cl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH2:24]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=1[O:31][C@@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@@H:10]1[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:21]1[CH:20]=[CH:19][CH:18]=[CH:23][CH:22]=1

参加物

7

反応物 4

HCID 996PhenolHCID 3283Diethyl EtherHCID 242162-BenzylphenolHCID 53697243(+/-)N-tert-butoxycarbonyl-1,2-iminoindane

生成物 1

HCID 18661286(+/-)cis-1-(2-Benzylphenoxy)-2-tert-butoxycarbonylaminoindane収率 24.8%

試薬・触媒・溶媒 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)触媒HCID 6212Chloroform溶媒

実験手順

A solution of (±) N-tert-butoxycarbonyl-1,2-iminoindane (2.33 g, 10 mmol), 2-hydroxy diphenylmethane (1.84 g, 10 mmol) and pyridinium p-toluenesulfonate (50 mg) in chloroform (100 ml) was heated at reflux for 3 h. On cooling, the solution was washed sequentially with aq. NaHCO3, water and then brine. After drying over Na2SO4, solvents were removed in vacuo and the resultant brown oil subjected to column chromatography on silica gel eluting with 10% diethyl ether in hexanes to afford a pale yellow oil which was a mixture of the desired adduct and the starting phenol. This mixture was taken up in 1:1 diethyl ether:pentane (200 ml) and washed three times with a 1:1 mixture of methanol and 10% aq. NaOH. After washing with water then brine, the organics were dried over Na2SO4 and then concentrated in vacuo. The residue was recrystallised to afford the title compound as a white solid (1.03 g) m.p. 113°-114.5° C. (from diethyl ether-pentane).

後処理

  1. temperatureat reflux for 3 h
  2. temperatureOn cooling
  3. washthe solution was washed sequentially with aq. NaHCO3, water
  4. dry with materialAfter drying over Na2SO4, solvents
  5. customwere removed in vacuo
  6. customto afford a pale yellow oil which
  7. washpentane (200 ml) and washed three times
  8. additionwith a 1:1 mixture of methanol and 10% aq. NaOH
  9. washAfter washing with water
  10. dry with materialbrine, the organics were dried over Na2SO4
  11. concentrationconcentrated in vacuo
  12. customThe residue was recrystallised

出典と根拠

ORDレコード
ord-6b6fd28f0b014cdc9aace03856d7fca4
出典データセット
uspto-grants-1998_06
特許番号
US05773463

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