Diethyl Ether → HCID 15512819, 화합물

HRID 1978830노트

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HRID 1978830 반응식
C([Li])CCC.BrC1C=[CH:11][C:10]([F:13])=[CH:9][C:8]=1OC.[CH2:16]([N:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:30]([O:32][CH2:33][CH3:34])C>>[CH2:16]([N:23]1[CH2:28][CH2:27][C:26]([C:8]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:34][C:33]=2[O:32][CH3:30])([OH:29])[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

5

반응물 4

HCID 3283Diethyl Ether3회HCID 192201-Benzyl-4-piperidoneHCID 70180432-Bromo-5-fluoroanisoleHCID 178418339Butyllithium

생성물 1

HCID 15512819HCID 15512819, 화합물수율 68%

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온도
-50 °C

실험 절차

To a solution of 9.8 mL (24 mmole) butyllithium (2.5M solution in hexane) in diethylether (20 mL) under N2 at −78° C. was slowly added 2-bromo-5-fluoroanisole (5.0 g, 24 mmole) in diethylether (5 mL). The mixture was allowed to warm up to −50° C. At this point, 1-benzyl-4-piperidone (4.62 g, 24.4 mmole) in diethylether (3 mL) was added. The resulting mixture was allowed to stirred at −50° C. for 30 minutes, and then warmed to room temperature. The reaction was quenched by dropwise addition of saturated NH4Cl solution. The mixture was then transferred to a separatory funnel, the layers were separated and the aqueous was extracted three times with EtOAc. The combined organic phase was dried over Na2SO4, filtered and concentrated. Flash chromatography (elution with 7:3 EtOAc-hexanes) afforded 5.27 g (68%) of 1-benzyl-4-(5-fluoro-2-methoxy-phenyl)-4-hydroxypiperidine as a yellow oil.

후처리

  1. customat −78° C.
  2. temperaturewarmed to room temperature
  3. customThe reaction was quenched by dropwise addition of saturated NH4Cl solution
  4. customThe mixture was then transferred to a separatory funnel
  5. customthe layers were separated
  6. extractionthe aqueous was extracted three times with EtOAc
  7. dry with materialThe combined organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washFlash chromatography (elution with 7:3 EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-b8fe06f957464bb99b7fd37bb1b8574f
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06239126B1

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