反应详情

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.

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