Trifluoroacetic acid → 2-Cyanoquinuclidine

HRID 1022968ノート

反応式

HRID 1022968 の反応式
[C:1]([CH:3](OS(C)(=O)=O)[CH2:4][CH:5]1[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6]1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[N:8]12[CH2:9][CH2:10][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]2[C:1]#[N:2]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 11695663HCID 11695663、化合物

生成物 1

HCID 1452092-Cyanoquinuclidine収率 39.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of tert-butyl 4-{2-cyano-2-[(methylsulfonyl)oxy]ethyl}piperidine-1-carboxylate (80.0 g) in dichloromethane (200 mL) was added a solution of trifluoroacetic acid (137.0 g) in dichloromethane (200 mL), and the reaction system was stirred at room temperature overnight. The reaction system was concentrated, acetonitrile (200 mL) was added to the residue, and triethylamine (98.0 g) was slowly added at 0° C. The mixture was concentrated, the residue was diluted with dichloromethane, and the mixture was washed with brine, and dried over anhydrous sodium sulfate. Insoluble material was removed by filtration, and the filtrate was concentrated. The residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (13.0 g) as a yellow oil.

後処理

  1. concentrationThe reaction system was concentrated
  2. additionacetonitrile (200 mL) was added to the residue, and triethylamine (98.0 g)
  3. additionwas slowly added at 0° C
  4. concentrationThe mixture was concentrated
  5. additionthe residue was diluted with dichloromethane
  6. washthe mixture was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customInsoluble material was removed by filtration
  9. concentrationthe filtrate was concentrated
  10. customThe residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-9e18d4a9b1314eff880c95eedfed5f96
出典データセット
uspto-grants-2014_05
特許番号
US08722660B2

反応ノート

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