Potassium Carbonate → 1-(2,2-Diphenylethyl)-3-methylpyrrolidin-3-ol

HRID 1496698

Reaktionsgleichung

Reaktionsgleichung von HRID 1496698
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][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)=O>C(#N)C>[C:22]1([CH:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:20][N:5]2[CH2:6][CH2:7][C:3]([CH3:2])([OH:8])[CH2:4]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 117478202,2-Diphenylethyl methanesulfonateHCID 533465593-Methylpyrrolidin-3-ol hydrochloride2×

Produkt 1

HCID 899618051-(2,2-Diphenylethyl)-3-methylpyrrolidin-3-olAusbeute 58,23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

According to Example 15, 3-methylpyrrolidin-3-ol hydrochloride was synthesized. To a 500 mL reaction flask were added 3-methylpyrrolidin-3-ol hydrochloride (11.46 g, 83 mmol), anhydrous potassium carbonate (28.75 g, 208 mmol) and acetonitrile (220 mL). To the resulting mixture was slowly added a solution of 2,2-diphenylethyl methanesulfonate (23 g, 83 mmol) in acetonitrile dropwisely at 85° C. The reaction was conducted for 12 hours. After the completion of reaction monitored by TLC, the resulting mixture 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. The crude product was purified by column chromatography (silica gel column, eluted with petroleum ether:ethyl acetate=30:1 (volumetric ratio)) to produce 1-(2,2-diphenylethyl)-3-methylpyrrolidin-3-ol (13.6 g) in a yield of 58.23%.

Aufarbeitung

  1. customwas synthesized
  2. customTo a 500 mL reaction flask
  3. customAfter the completion of reaction
  4. customthe resulting mixture was evaporated under reduced pressure
  5. customto remove acetonitrile
  6. additionA mixed solution of dichloromethane and water was added for extraction
  7. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  8. customevaporated
  9. customto remove the solvent
  10. customto produce a crude product
  11. customThe crude product was purified by column chromatography (silica gel column, eluted with petroleum ether:ethyl acetate=30:1 (volumetric ratio))

Quellen und Nachweise

ORD-Eintrag
ord-e8ed6fa782a14dee921fc287f6951eb8
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09198902B2

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