Acetic Acid → 5-Methanesulfonyloxy-1,2,3,4-tetrahydroquinoline

HRID 1649419ノート

反応式

HRID 1649419 の反応式
[CH3:1][S:2]([O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10](=O)[NH:11]2)(=[O:4])=[O:3].[BH4-].[Na+].C(O)(=O)C>O1CCOCC1>[CH3:1][S:2]([O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][NH:11]2)(=[O:3])=[O:4]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 128996762-Oxo-1,2,3,4-tetrahydroquinolin-5-yl methanesulfonate

生成物 1

HCID 128996785-Methanesulfonyloxy-1,2,3,4-tetrahydroquinoline収率 44.8%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

4.5 g of 5-methanesulfonyloxy-3,4-dihydrocarbostyril was suspended in 90 ml of dioxane and 35 g of NaBH4 was added to the suspension then 5.3 ml of acetic acid was added dropwise to the mixture. After heat-refluxing the resulting mixture for 1 hour the solvent was removed under reduced pressure. A saturated aqueous solution of sodium bicarbonate was added to the residue to form precipitates which were filtered and washed with chloroform. The filtrate was extracted with chloroform and the chloroform layer was dried over Na2SO4 followed by removing the solvent. The residue was purified through a silica gel column chromatography (silica gel: Wako C-200, a trade name for a product of Wako Junyaku Co., Ltd.; eluent: chloroform) and the eluate thus-obtained was crystallized from petroleum ether. Recrystallization of the crystals thus-obtained from methanol gave 1.9 g of 5-methanesulfonyloxy-1,2,3,4-tetrahydroquinoline, colorless prisms having a melting point of 74° to 76° C.

後処理

  1. temperatureAfter heat-refluxing the resulting mixture for 1 hour the solvent
  2. customwas removed under reduced pressure
  3. additionA saturated aqueous solution of sodium bicarbonate was added to the residue
  4. customto form
  5. customprecipitates which
  6. filtrationwere filtered
  7. washwashed with chloroform
  8. extractionThe filtrate was extracted with chloroform
  9. dry with materialthe chloroform layer was dried over Na2SO4
  10. customby removing the solvent
  11. customThe residue was purified through a silica gel column chromatography (silica gel
  12. customeluent: chloroform) and the eluate thus-obtained
  13. customwas crystallized from petroleum ether
  14. customRecrystallization of the crystals
  15. customthus-obtained from methanol

出典と根拠

ORDレコード
ord-11f123434994445ca1977c3562e2aae2
出典データセット
uspto-grants-1983_11
特許番号
US04416884

反応ノート

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