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p-Toluenesulfonic acid → (1R,2R)-1-[3-(tertbutyldiphenylsilyloxy)benzyl]-1,2-dihydroxycyclohexane

HRID 379312
ノート
印刷プレビュー

反応式

HRID 379312 の反応式
CC1(C)[O:6][C@@H:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C@:4]2([CH:11](O)[C:12]2[CH:13]=[C:14]([O:18][Si:19]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:15]=[CH:16][CH:17]=2)[O:3]1.C1C=CC(OC(Cl)=S)=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.C1(C)C=CC=CC=1.C([SnH](CCCC)CCCC)CCC.CO.C1COCC1.N1C=CC=CC=1>[C:32]([Si:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[O:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[CH2:11][C@:4]1([OH:3])[CH2:10][CH2:9][CH2:8][CH2:7][C@H:5]1[OH:6])([CH3:35])([CH3:33])[CH3:34]
参加物実験手順後処理出典と根拠反応ノート

参加物

11

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 6547AzobisisobutyronitrileHCID 70498Phenyl thioxochloroformateHCID 206917043-[((3aR,7aR)-2,2-dimethyl-hexahydro-1,3-benzodioxol-3a-yl) hydroxymethyl]-1-(tertbutyldiphenyl-silyloxy)benzene

生成物 1

HCID 20691700(1R,2R)-1-[3-(tertbutyldiphenylsilyloxy)benzyl]-1,2-dihydroxycyclohexane収率 74.8%

試薬・触媒・溶媒 6

HCID 887Methanol溶媒HCID 1049Pyridine溶媒HCID 1140Toluene溶媒HCID 5948Tributylstannane溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-[((3aR,7aR)-2,2-dimethyl-hexahydro-1,3-benzodioxol-3a-yl) hydroxymethyl]-1-(tertbutyldiphenyl-silyloxy)benzene (45 g) in CH2Cl2 (450 ml) were added phenyl chlorothionoformate (14.5 ml) and pyridine (18 ml) at 0° C. After being stirred for 12 hours at room temperature, the mixture was evaporated and the resultant was partitioned between EtOAc and water. The organic layer was washed with water, 1N-HCl solution, sat.NaHCO3 solution and then brine. The solvent was evaporated in vacuo to give an oily residue. The residue was dissolved in toluene (400 ml) to which tributyltinhydride (50 ml) and 2,2′-azobis-(isobutyronitrile)(100 mg) were added. The mixture was refluxed for 4 hours under stirring and then purified by chromatography on silica gel to give an oily compound. The oily compound was dissolved in a mixture of MeOH (200 ml) and THF (100 ml), to which p-toluenesulphonic acid (200mg) was added at room temperature. The mixture was stirred for 12 hours and evaporated. The residue was partitioned between EtOAc and water. The organic layer was washed with water, sat. NaHCO3 solution and then brine. The solvent was evaporated in vacuo to give (1R,2R)-1-[3-(tertbutyldiphenylsilyloxy)benzyl]-1,2-dihydroxycyclohexane (30 g).

後処理

  1. customthe mixture was evaporated
  2. customthe resultant was partitioned between EtOAc and water
  3. washThe organic layer was washed with water, 1N-HCl solution
  4. customThe solvent was evaporated in vacuo
  5. customto give an oily residue
  6. additionwere added
  7. temperatureThe mixture was refluxed for 4 hours
  8. stirringunder stirring
  9. custompurified by chromatography on silica gel
  10. customto give an oily compound
  11. additionwas added at room temperature
  12. stirringThe mixture was stirred for 12 hours
  13. customevaporated
  14. customThe residue was partitioned between EtOAc and water
  15. washThe organic layer was washed with water, sat. NaHCO3 solution
  16. customThe solvent was evaporated in vacuo

出典と根拠

ORDレコード
ord-bddf0593e23e4af9993784d751d442f2
出典データセット
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06297267B1

反応ノート

読み込み中…

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