Reaction #44486

Reaction equation

solution

4-(tert-Butyl-dimethyl-silanyloxymethyl)-1-cycloheptyl-3,3-dimethyl-pyrrolidin-2-one

Dess-Martin periodinane

→

title compound

1-Cycloheptyl-4,4-dimethyl-5-oxo-pyrrolidine-3-carbaldehyde

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe solvent was evaporated in vacuo
2. 2
   workup.STIRRINGstirred at room temperature for two hours
3. 3
   OtherThe reaction was quenched with 10% sodium bisulfite
4. 4
   Extractionextracted with dichloromethane
5. 5
   WashThe organic phase was washed with water
6. 6
   Dryingdried with MgSO4
7. 7
   Filtrationfiltered
8. 8
   Otherevaporated in vacuo

Procedure

To a solution of Example 1D (0.168 mg, 0.475 mmoles) in methanol (1.5 mL), two drops of 12M HCl was added and stirred for one hour. The solvent was evaporated in vacuo. The residue was taken in dichloromethane (2.5 mL) and Dess-Martin periodinane (0.25 gm, 0.593 mmoles) was added and stirred at room temperature for two hours. The reaction was quenched with 10% sodium bisulfite and extracted with dichloromethane. The organic phase was washed with water, dried with MgSO4, filtered, and evaporated in vacuo to provide the title compound.

Source