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

HRID 2245409노트

반응식

HRID 2245409 반응식
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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0cf271395e7149a79d2ca9109ee47fad
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07683056B2

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