Ethyl (3R)-5-oxo4-(phenylmethyl)-3-morpholinecarboxylate → (R)-Ethyl 4-benzylmorpholine-3-carboxylate

HRID 2245409ノート

反応式

HRID 2245409 の反応式
O=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:5][O:4][CH2:3]1>C1COCC1>[C:9]1([CH2:8][N:7]2[CH2:2][CH2:3][O:4][CH2:5][C@@H:6]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

3

反応物 1

HCID 13543380Ethyl (3R)-5-oxo4-(phenylmethyl)-3-morpholinecarboxylate

生成物 1

HCID 13543384(R)-Ethyl 4-benzylmorpholine-3-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The title Compound was prepared according to the procedure used by G. R. Brown, J. Chem. Soc. Perkin Trans 1, 1985, 2577, using ethyl (3R)-5-oxo-4-(phenylmethyl) -3-morpholinecarboxylate (D45, 3.64 g, 13.84 mmol) in dry THF (70 mL), cooled in an ice bath before adding borane-dimethylsulphide complex (1.84 mL, 10M), slowly. The reaction mixture was allowed to warm up to room temperature overnight. Stirred for further six hours, added more borane-dimethylsulphide complex and stirred at R.T. over the weekend. Reaction quenched carefully with water, dropwise till the effervescence had finished. Solvent evaporated. Residue dissolved in water, basified to pH ˜10 using 2N NaOH solution before extracting with Et2O. Organic layer was then extracted with 2N HCl solution. Acid layer was then basified using 2N NaOH solution before extracting with Et2O ×3. Combined extracts were dried (MgSO4). Filtered. Evaporated under reduced pressure to afford the title compound as a colurless oil in a 68% yield.

後処理

  1. customThe title Compound was prepared
  2. temperaturecooled in an ice bath
  3. additionbefore adding borane-dimethylsulphide complex (1.84 mL, 10M)
  4. additionadded more borane-dimethylsulphide complex
  5. stirringstirred at R.T. over the weekend
  6. customReaction
  7. customquenched carefully with water, dropwise till the effervescence
  8. customSolvent evaporated
  9. dissolutionResidue dissolved in water
  10. extractionbefore extracting with Et2O
  11. extractionOrganic layer was then extracted with 2N HCl solution
  12. extractionbefore extracting with Et2O ×3
  13. dry with materialCombined extracts were dried (MgSO4)
  14. filtrationFiltered
  15. customEvaporated under reduced pressure

出典と根拠

ORDレコード
ord-0cf271395e7149a79d2ca9109ee47fad
出典データセット
uspto-grants-2010_03
特許番号
US07683056B2

反応ノート

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