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

HRID 421191Notes

Reaction equation

HRID 421191 reaction equation
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

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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, 10 M), 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 colorless oil in a 68% yield.

Workup

  1. customThe title Compound was prepared
  2. temperaturecooled in an ice bath
  3. additionbefore adding borane-dimethylsulphide complex (1.84 mL, 10 M)
  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

Sources & evidence

ORD record
ord-e101b58af39b49cdb57050dd0b492af4
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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