반응 #467293

반응 방정식

(2R)-N-benzyloxycarbonylproline

benzoin

1-ethyl 3-(3-dimethylaminopropyl)carbodiimide

dimethylaminopyridine

→

(2R)-1-benzyloxycarbonyl-2-(4,5-diphenyloxazol-2-yl)pyrrolidine

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타the solvent was evaporated in vacuo
2. 2
   기타the residue was partitioned between ethyl acetate and water
3. 3
   세척The organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine
4. 4
   건조dried over MgSO4
5. 5
   기타evaporated in vacuo
6. 6
   workup.DISSOLUTIONThe obtained compound and CH3COONH4 (8.2 g) were dissolved in acetic acid (50 ml)
7. 7
   workup.STIRRINGthe mixture was stirred for 4 hours at 100° C
8. 8
   기타After the solvent was removed
9. 9
   기타the residue was partitioned between ethyl acetate and water
10. 10
    세척The organic layer was washed with water, sat. NaHCO3 and brine
11. 11
    기타The dried solvent was evaporated in vacuo
12. 12
    기타the residue was purified by chromatography on silica gel

실험 절차

To a solution of (2R)-N-benzyloxycarbonylproline (5 g) in CH2Cl2 (50 ml) were added benzoin (4.5 g), 1-ethyl 3-(3-dimethylaminopropyl)carbodiimide (3.9 ml), and dimethylaminopyridine (2.6 g) at room temperature under N2. After being stirred for 12 hours at room temperature, the solvent was evaporated in vacuo, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The obtained compound and CH3COONH4 (8.2 g) were dissolved in acetic acid (50 ml) and the mixture was stirred for 4 hours at 100° C. After the solvent was removed, the residue was partitioned between ethyl acetate and water. The organic layer was washed with water, sat. NaHCO3 and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give (2R)-1-benzyloxycarbonyl-2-(4,5-diphenyloxazol-2-yl)pyrrolidine (4 g).

출처