Reaction #1583875

Reaction equation

3-methylpyrrolidin-3-ol hydrochloride

potassium carbonate

3,3-diphenylpropyl methanesulfonate

→

1-(3,3-diphenylpropyl)-3-methylpyrrolidin-3-ol

Yield 57.0%

Solvents

acetonitrile

acetonitrile

Conditions

Workup

1. 1
   OtherTo a 10 L reaction flask
2. 2
   OtherAfter the completion of reaction
3. 3
   Otherthe reaction solution was evaporated under reduced pressure
4. 4
   Otherto remove acetonitrile
5. 5
   workup.ADDITIONA mixed solution of dichloromethane and water was added for extraction
6. 6
   DryingThe organic phase was dried over anhydrous sodium sulfate
7. 7
   Otherevaporated
8. 8
   Otherto remove the solvent
9. 9
   Otherto produce a crude product, which
10. 10
    Otherwas purified by column chromatography (silica gel column, eluted with petroleum ether: ethyl acetate=50:1 (volumetric ratio))

Procedure

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%.

Source