Water → Tert-butyl 4-(1-cyano-2-oxoethyl)piperidine-1-carboxylate

HRID 1616076노트

반응식

HRID 1616076 반응식
[C:1]([CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#[N:2].C[C:18](C)([O-:20])C.[K+].C(OCC)=O.O>CN(C)C=O>[C:1]([CH:3]([CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1)[CH:18]=[O:20])#[N:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 8025Ethyl formateHCID 22248390tert-Butyl 4-(cyanomethyl)piperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 86681870Tert-butyl 4-(1-cyano-2-oxoethyl)piperidine-1-carboxylate수율 93.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Under an argon atmosphere, tert-butyl 4-(cyanomethyl)piperidine-1-carboxylate (2.24 g, 10 mmol) and potassium tert-butoxide (6.73 g, 60 mmol) were dissolved in anhydrous N,N-dimethyl formamide (15 mL), and a solution of ethyl formate (4.44 g, 60 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added dropwise under ice-cooling. The temperature was gradually raised to room temperature, and then the resultant mixture was stirred overnight. Water was added to the reaction liquid, followed by extraction with ethyl acetate. 1 N hydrochloric acid was added to the obtained aqueous layer until it reached a pH of 6, and then the resultant mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure to give tert-butyl 4-(1-cyano-2-oxoethyl)piperidine-1-carboxylate (2.35 g) as a crude product.

후처리

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. addition1 N hydrochloric acid was added to the obtained aqueous layer until it
  4. extractionthe resultant mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under a reduced pressure

출처 및 근거

ORD 기록
ord-d364429de8bf43caa335d4507d73cf59
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765771B2

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