반응 #678527

반응 방정식

Na2CO3

NaBH(OAc)3

6-fluoroindoline

1-Boc-4-piperidone

→

tert-butyl 4-(6-fluoroindolin-1-yl)piperidine-1-carboxylate

용매

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting mixture was stirred at room temperature for 24 h
2. 2
   workup.STIRRINGAfter 30 min stirring
3. 3
   기타the layers were separated
4. 4
   추출The aqueous layer was extracted with CH2Cl2 (100 mL)
5. 5
   세척The combined organic layer was washed with brine (100 mL)
6. 6
   건조dried (Na2SO4)
7. 7
   여과filtered
8. 8
   기타The solvent was removed by roto-evaporator, Et2O (10 mL)
9. 9
   workup.ADDITIONhexane (150 mL) were added to the resulting residue
10. 10
    기타resulting in the formation of a white solid, which
11. 11
    기타was collected
12. 12
    세척washed with 5% Et2O/hexane
13. 13
    기타dried

실험 절차

To a solution of 6-fluoroindoline (9.36 g, 68 mmol) in CH2Cl2 (100 mL) was added 1-Boc-4-piperidone (13.6 g, 68 mmol). The resulting mixture was stirred at room temperature for 1 h and NaBH(OAc)3 (18 g, 85 mmol, 1.25 equiv) was added. The resulting mixture was stirred at room temperature for 24 h and was then poured slowly to a vigorously stirred Na2CO3(aq). After 30 min stirring, the layers were separated. The aqueous layer was extracted with CH2Cl2 (100 mL). The combined organic layer was washed with brine (100 mL), dried (Na2SO4), and filtered. The solvent was removed by roto-evaporator, Et2O (10 mL) and then hexane (150 mL) were added to the resulting residue. The mixture was allowed to stand, resulting in the formation of a white solid, which was collected and washed with 5% Et2O/hexane and then dried. This was repeated to yield three crops of tert-butyl 4-(6-fluoroindolin-1-yl)piperidine-1-carboxylate as a white solid.

출처