Potassium Carbonate → 1-(3,3-Diphenylpropyl)-3-methylpyrrolidin-3-ol

HRID 1496693

반응식

HRID 1496693 반응식
Cl.[CH3:2][C:3]1([OH:8])[CH2:7][CH2:6][NH:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:20][CH2:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=O)=O>C(#N)C>[C:23]1([CH:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:21][CH2:20][N:5]2[CH2:6][CH2:7][C:3]([CH3:2])([OH:8])[CH2:4]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 222382923,3-Diphenylpropyl methanesulfonateHCID 533465593-Methylpyrrolidin-3-ol hydrochloride

생성물 1

HCID 899617461-(3,3-Diphenylpropyl)-3-methylpyrrolidin-3-ol수율 57%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

To a 10 L reaction flask were added 3-methylpyrrolidin-3-ol hydrochloride (616 g, 4.48 mol), anhydrous potassium carbonate (1186 g, 8.6 mol) and acetonitrile (5 L). To the resulting mixture was slowly added a solution of 3,3-diphenylpropyl methanesulfonate (1000 g, 3.45 mol) in acetonitrile dropwisely at 85° C. The reaction was conducted for 12 hours. After the completion of reaction monitored by TLC, the reaction solution was evaporated under reduced pressure to remove acetonitrile. A mixed solution of dichloromethane and water was added for extraction. The organic phase was dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce a crude product, which was purified by column chromatography (silica gel column, eluted with petroleum ether: ethyl acetate=50:1 (volumetric ratio)) to produce 1-(3,3-diphenylpropyl)-3-methylpyrrolidin-3-ol (580 g) in a yield of 57%.

후처리

  1. customTo a 10 L reaction flask
  2. customAfter the completion of reaction
  3. customthe reaction solution was evaporated under reduced pressure
  4. customto remove acetonitrile
  5. additionA mixed solution of dichloromethane and water was added for extraction
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. customevaporated
  8. customto remove the solvent
  9. customto produce a crude product, which
  10. customwas purified by column chromatography (silica gel column, eluted with petroleum ether: ethyl acetate=50:1 (volumetric ratio))

출처 및 근거

ORD 기록
ord-46599b8306124f56911108474c6cb3f3
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09198902B2

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