Dimethyl Sulfoxide → Benzyl 4-(2-azido-3,3,3-trifluoropropoxy)piperidine-1-carboxylate

HRID 2368104노트

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HRID 2368104 반응식
[F:1][C:2]([F:28])([F:27])[CH:3](OS(C)(=O)=O)[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1.[N-:29]=[N+:30]=[N-:31].[Na+].CS(C)=O>O>[N:29]([CH:3]([C:2]([F:28])([F:27])[F:1])[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1)=[N+:30]=[N-:31]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 86658699Benzyl 4-{3,3,3-trifluoro-2-[(methylsulfonyl)oxy]propoxy}piperidine-1-carboxylate

생성물 1

HCID 86658700Benzyl 4-(2-azido-3,3,3-trifluoropropoxy)piperidine-1-carboxylate수율 25.6%

시약·촉매·용매 1

HCID 962Water용매

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온도
100 °C

실험 절차

A mixture of benzyl 4-{3,3,3-trifluoro-2-[(methylsulfonyl)oxy]propoxy}piperidine-1-carboxylate (1.31 g), sodium azide (1.00 g), 15-crown-5-ether (3.39 g) and dimethyl sulfoxide (5 mL) was stirred at 100° C. for 3 days. Water was added thereto, and the obtained mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (294 mg).

후처리

  1. extractionthe obtained mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-2be79847caf444ccb0b82b8f22b1b84a
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703758B2

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