Trifluoroacetic acid → 2-Cyanoquinuclidine

HRID 1022968노트

반응식

HRID 1022968 반응식
[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]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 11695663HCID 11695663, 화합물

생성물 1

HCID 1452092-Cyanoquinuclidine수율 39.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9e18d4a9b1314eff880c95eedfed5f96
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722660B2

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