تفاعل #44499

معادلة التفاعل

Tetrabutyl ammonium fluoride

solution

9-[4-(tert-Butyl-diphenyl-silanyloxymethyl)-3 3-dimethyl-2-oxo-pyrrolidin-1-yl]-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

→

title product

9-(4-Hydroxymethyl-3,3-dimethyl-2-oxo-pyrrolidin-1-yl)-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىpartitioned with ethyl acetate and water
2. 2
   غسيلThe organic phase was washed with brine
3. 3
   تجفيفdried (MgSO4)
4. 4
   ترشيحfiltered
5. 5
   أخرىevaporated
6. 6
   أخرىThe residue was purified over silica gel using 20-100% ethyl acetate in hexanes

الإجراء التجريبي

Tetrabutyl ammonium fluoride (3.2 mL, 1 M in tetrahydrofuran, 3.2 mmol) was added to a stirred solution of Example 7C (0.9 g, 1.56 mmol) in tetrahydrofuran 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 title product as a white solid.

المصدر