반응 #81469

반응 방정식

HCl

4-cyano-1-[2-(4-fluorophenyl)ethyl]piperidine

DIBAL-H

NaOH

→

1-[2-(4-fluorophenyl)ethyl]-4-piperidinecarboxaldehyde

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   추출extracted 2x with ether
3. 3
   세척The combined organic layers were washed with brine
4. 4
   건조dried (MgSO4)
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타to afford a pale yellow oil
8. 8
   기타The oil was chromatographed on silica gel a eluting with EtOAc
9. 9
   기타evaporated
10. 10
    기타to afford an oil
11. 11
    workup.DISTILLATIONThis oil was distilled (b.p. 166° C., 0.05 mm Hg)

실험 절차

To a stirred solution of 4-cyano-1-[2-(4-fluorophenyl)ethyl]piperidine (1.00 g, 4.3 mmol) in THF (20 mL) under argon at 0° C. was added DIBAL-H (4.6 mL of a 1.0M solution in THF, 4.6 mmol) via syringe. After stirring overnight at room temperature 10% aqueous HCl (25 mL) was added and the solution was stirred for 3 hours. The entire mixture was then poured into 10% aqueous NaOH (50 mL), then extracted 2x with ether. The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated to afford a pale yellow oil. The oil was chromatographed on silica gel a eluting with EtOAc. The appropriate fractions were combined and evaporated to afford an oil. This oil was distilled (b.p. 166° C., 0.05 mm Hg) to afford 1-[2-(4-fluorophenyl)ethyl]-4-piperidinecarboxaldehyde, obtained as a colorless oil. Anal. Calcd for C14H18FNO: C, 71.46; H, 7.71; N, 5.95. Found: C, 71.08, H, 7.81; N, 5.86.

출처