반응 #972008

반응 방정식

(R)-cyclopentylhydroxyphenyl acetic acid

t-butyl 1-piperazinecarboxylate

DIPEA

HOBt

EDCI

→

title compound

수율 68.7%

(R)-2-Cyclopentyl-2-hydroxy-2-phenyl-1-piperazin-1-ylethanone

수율 68.7%

용매

DCM

반응 조건

후처리

1. 1
   세척The mixture was then washed with 1N NaOH (300 mL), 1N HCl (300 mL)
2. 2
   건조The organic layer was dried over MgSO4
3. 3
   여과filtered
4. 4
   기타The solvent was removed by rotary evaporation
5. 5
   workup.ADDITIONA solution of 20% TFA/DCM was added to the crude material
6. 6
   workup.STIRRINGthe resulting mixture was stirred for 2 hours at room temperature
7. 7
   기타The solvent was removed by rotary evaporation
8. 8
   workup.ADDITIONDCM (300 mL) was added
9. 9
   세척the mixture was washed with saturated sodium bicarbonate (300 mL)
10. 10
    기타The organic layer was then removed
11. 11
    건조dried over MgSO4
12. 12
    여과filtered
13. 13
    기타The crude material was purified by silica gel chromatography (10% MeOH/DCM with 1% NH3 (aq))

실험 절차

To a stirred solution of (R)-cyclopentylhydroxyphenyl acetic acid (10.0 g, 45.4 mmol) in DCM (200 mL) was added t-butyl 1-piperazinecarboxylate (8.5 g, 45.4 mmol). DIPEA (23.7 mL, 13.6 mmol) and HOBt (10.4 g, 68.1 mmol) were added to the mixture, followed by EDCI (10.4 g, 54.5 mmol). The mixture was stirred at room temperature for 12 hours. The mixture was then washed with 1N NaOH (300 mL), 1N HCl (300 mL), and then saturated aqueous NaCl (300 mL). The organic layer was dried over MgSO4 and filtered. The solvent was removed by rotary evaporation. A solution of 20% TFA/DCM was added to the crude material, and the resulting mixture was stirred for 2 hours at room temperature. The solvent was removed by rotary evaporation. DCM (300 mL) was added and the mixture was washed with saturated sodium bicarbonate (300 mL). The organic layer was then removed, dried over MgSO4 and filtered. The crude material was purified by silica gel chromatography (10% MeOH/DCM with 1% NH3 (aq)) to afford the title compound as a white powder (9.0 g, 31.2 mmol).

출처