Reaction #44496

Reaction equation

Tetrabutyl ammonium fluoride

product

4-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(5-hydroxy-cyclooctyl)-3,3-dimethyl-pyrrolidin-2-one

→

titled product

1-(5-Hydroxy-cyclooctyl)-4-hydroxymethyl-3 3-dimethyl-pyrrolidin-2-one

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Otherpartitioned with ethyl acetate and water
2. 2
   WashThe organic phase was washed with brine
3. 3
   Dryingdried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated
6. 6
   OtherThe residue was purified over silica gel using 20-100% ethyl acetate in hexanes

Procedure

Tetrabutyl ammonium fluoride (0.76 mL, 1 M in tetrahydrofuran, 0.76 mmol) was added to a stirred solution of the product of Example 5J (0.30 g, 0.60 mmol) in tetrahydrofuran (5 mL) at room temperature. The resulting solution was stirred for two hours and then partitioned with ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4), filtered, and evaporated. The residue was purified over silica gel using 20-100% ethyl acetate in hexanes to give the titled product as a white solid.

Source