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

HRID 1803215ノート

反応式

HRID 1803215 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2d753441dc3c47a698156e0846da5c66
出典データセット
uspto-grants-2013_01
特許番号
US08349880B2

反応ノート

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