Reaction #1583880

Reaction equation

3-methylpyrrolidin-3-ol hydrochloride

3-methylpyrrolidin-3-ol hydrochloride

potassium carbonate

2,2-diphenylethyl methanesulfonate

→

1-(2,2-diphenylethyl)-3-methylpyrrolidin-3-ol

Yield 58.2%

Solvents

acetonitrile

acetonitrile

Conditions

Workup

1. 1
   Otherwas synthesized
2. 2
   OtherTo a 500 mL reaction flask
3. 3
   OtherAfter the completion of reaction
4. 4
   Otherthe resulting mixture was evaporated under reduced pressure
5. 5
   Otherto remove acetonitrile
6. 6
   workup.ADDITIONA mixed solution of dichloromethane and water was added for extraction
7. 7
   DryingThe organic phase was dried over anhydrous sodium sulfate
8. 8
   Otherevaporated
9. 9
   Otherto remove the solvent
10. 10
    Otherto produce a crude product
11. 11
    OtherThe crude product was purified by column chromatography (silica gel column, eluted with petroleum ether:ethyl acetate=30:1 (volumetric ratio))

Procedure

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%.

Source