Reaction #1583887

Reaction equation

3-methylpyrrolidin-3-ol hydrochloride

potassium carbonate

diphenylbromomethane

→

1-(diphenylmethyl)-3-methylpyrrolidin-3-ol

Yield 52.0%

Solvents

acetonitrile

acetonitrile

Conditions

Workup

1. 1
   OtherAfter the completion of reaction
2. 2
   Otherthe resulting mixture was evaporated under reduced pressure
3. 3
   Otherto remove acetonitrile
4. 4
   workup.ADDITIONTo the residue was added a mixed solution of dichloromethane and water
5. 5
   Extractionfor 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
10. 10
    OtherThe crude product was purified by column chromatography (silica gel column, eluted with petroleum ether:ethyl acetate=30:1 (volumetric ratio))

Procedure

To a reaction flask were added 3-methylpyrrolidin-3-ol hydrochloride (1 g, 7.2 mmol), anhydrous potassium carbonate (2.5 g, 18 mmol) and acetonitrile (50 L). To the resulting mixture was slowly added a solution of diphenylbromomethane (1.78 g, 7.2 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. To the residue was added a mixed solution of dichloromethane and water 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-(diphenylmethyl)-3-methylpyrrolidin-3-ol (1 g) in a yield of 52.0%.

Source