Dimethyl Sulfoxide → Benzyl 4-(oxiran-2-ylmethoxy)piperidine-1-carboxylate

HRID 2368105노트

반응식

HRID 2368105 반응식
[I-].C[S+](C)(C)=O.[H-].[Na+].[CH3:9]S(C)=O.[O:13]=[CH:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:19][CH2:18]1>O>[O:13]1[CH2:9][CH:14]1[CH2:15][O:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])[CH2:19][CH2:18]1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 57517496Benzyl 4-(2-oxoethoxy)piperidine-1-carboxylate

생성물 1

HCID 57517497Benzyl 4-(oxiran-2-ylmethoxy)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of trimethylsulfoxonium iodide (2.17 g), sodium hydride (oil, 60%, 395 mg) and dimethyl sulfoxide (20 mL) was stirred at room temperature for 1 hr, and benzyl 4-(2-oxoethoxy)piperidine-1-carboxylate (2.28 g) was added thereto. The obtained mixture was stirred at room temperature 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 (208 mg).

후처리

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

출처 및 근거

ORD 기록
ord-01546043d50c4dd69623995b65c502da
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703758B2

반응 노트

불러오는 중…