5-(2-(Tert-butoxycarbonyl)hydrazono)-5-(4-fluorophenyl)pentanoic acid → Tert-butyl 2-(4-fluorophenyl)-6-oxopiperidin-1-ylcarbamate

HRID 1803215노트

반응식

HRID 1803215 반응식
[C:1]([O:5][C:6]([NH:8][N:9]=[C:10]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[CH2:11][CH2:12][CH2:13][C:14](O)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH:10]2[CH2:11][CH2:12][CH2:13][C:14](=[O:15])[N:9]2[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:18][CH:19]=1

참가 물질

4

반응물 1

HCID 866499235-(2-(Tert-butoxycarbonyl)hydrazono)-5-(4-fluorophenyl)pentanoic acid

생성물 1

HCID 66859411Tert-butyl 2-(4-fluorophenyl)-6-oxopiperidin-1-ylcarbamate수율 55%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

Step AAG (2): 10% Palladium on carbon (0.5 g) was carefully added to a solution of 5-(2-(tert-Butoxycarbonyl)hydrazono)-5-(4-fluorophenyl)pentanoic acid (2.3 g, 7.09 mmol) in MeOH (30 mL) in a Parr hydrogenation bottle under nitrogen. The bottle was repeatedly evacuated and flushed with H2 gas (50 psi). The mixture was shaken for 5 h. The vessel was flushed with nitrogen. The reaction contents were filtered through diatomaceous earth (Celite®). The plug and vessel were washed with fresh methanol. The filtrates were combined and concentrated in vacuo. The crude product was purified using silica gel column chromatography (10-80, EtOAc/chloroform, linear gradient) to afford tert-butyl 2-(4-fluorophenyl)-6-oxopiperidin-1-ylcarbamate (1.2 g, 55% yield). 1H NMR (500 MHz, chloroform-d) δ ppm 7.13-7.20 (an, 2 H) 7.06 (t, J=8.55 Hz, 2 H) 6.40 (br. s., 1 H) 4.91 (br. s., 1 H) 2.52-2.75 (m, 2 H) 2.20-2.40 (m, 1 H) 1.77-1.93 (m, 3 H) 1.44 (s, 9 H).

후처리

  1. customThe bottle was repeatedly evacuated
  2. customflushed with H2 gas (50 psi)
  3. customThe vessel was flushed with nitrogen
  4. customThe reaction contents
  5. filtrationwere filtered through diatomaceous earth (Celite®)
  6. washThe plug and vessel were washed with fresh methanol
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified

출처 및 근거

ORD 기록
ord-2d753441dc3c47a698156e0846da5c66
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349880B2

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