Potassium Carbonate → Ethyl 1-benzyl-4-(cyanomethyl)-3-oxopiperidine-4-carboxylate

HRID 1848474노트

반응식

HRID 1848474 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10](=[O:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]#[N:29]>CC(C)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:27][C:28]#[N:29])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10](=[O:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 419705Ethyl 3-oxo-1-(phenylmethyl)-4-piperidinecarboxylate

생성물 1

HCID 86709485Ethyl 1-benzyl-4-(cyanomethyl)-3-oxopiperidine-4-carboxylate

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a flask charged with ethyl 1-benzyl-3-oxopiperidine-4-carboxylate (1.0 g, 3.8 mmol) and a stir bar was added K2CO3 (1.06 g, 7.6 mmol), bromoacetonitrile (0.92 g, 7.6 mmo0, and acetone (15 mL). The reaction was allowed to stir at RT for 2 hours. LC showed slow reaction. It was then heated to 45° C. for 3 hours. LC showed complete reaction at that point. The reaction was quenched with NH4Cl, extracted with EtOAc, dried over Na2SO4, filtered and concentrated. The crude product was purified by MPLC to furnish the title compound. LCMS: m/z 301 (M+H)+.

후처리

  1. customreaction
  2. temperatureIt was then heated to 45° C. for 3 hours
  3. customreaction at that point
  4. customThe reaction was quenched with NH4Cl
  5. extractionextracted with EtOAc
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by MPLC

출처 및 근거

ORD 기록
ord-1cb8f7b72b2542d2840e9882b42b44a7
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952166B2

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