Sulfuric Acid → Ethyl [(6S)-6-(3,5-difluorophenyl)-3,3-dimethyl-2,4-dioxopiperidin-1-yl]acetate

HRID 1866658ノート

反応式

HRID 1866658 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:13](=[O:21])[C:12]([CH3:23])([CH3:22])[C@@H:11]([OH:24])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.OS(O)(=O)=O>CC(C)=O.O.[O-2].[O-2].[O-2].[Cr+6]>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:13](=[O:21])[C:12]([CH3:23])([CH3:22])[C:11](=[O:24])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

参加物

6

反応物 2

HCID 1118Sulfuric AcidHCID 86616394HCID 86616394、化合物2 回

生成物 1

HCID 86616396Ethyl [(6S)-6-(3,5-difluorophenyl)-3,3-dimethyl-2,4-dioxopiperidin-1-yl]acetate

試薬・触媒・溶媒 3

HCID 10219390chromium (VI) trioxide触媒HCID 180Acetone溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To a solution of ethyl [(4S,6S)-6-(3,5-difluorophenyl)-4-hydroxy-3,3-dimethyl-2-oxopiperidin-1-yl]acetate (470 mg, 1.377 mmol, described in Intermediate 21) in acetone (24 mL) at 0° C. was added a solution of chromium (VI) trioxide (174 mg, 1.740 mmol) in H2O (0.5 mL) and H2SO4 (0.147 mL, 2.75 mmol), in three portions over 5 min and the mixture was stirred at 0° C. for 30 min. Most of the acetone was removed by concentration in vacuo, and the residue was basified with saturated aqueous NaHCO3 (75 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine (40 mL) and dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:CH3OH—100:0 to 92:8, to give the title compound. MS: m/z=340 (M+1).

後処理

  1. customMost of the acetone was removed by concentration in vacuo
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic layers were washed with brine (40 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of CH2Cl2

出典と根拠

ORDレコード
ord-69a7cdb2f6b54d1b9c9972eb3e664c66
出典データセット
uspto-grants-2009_12
特許番号
US07629338B2

反応ノート

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