Reaction #157829

Reaction equation

(5R)-5-[(E)-2-(5-amino-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

sodium bicarbonate

→

(5R)-5-[(E)-2-(5-amino-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one

Yield 44.0%

Solvents

trifluoroacetic acid

anisole

Conditions

Workup

1. 1
   Extractionfollowed by extraction with ethyl acetate
2. 2
   WashThe organic layer was washed with brine
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   Otherafter which the solvent was evaporated under reduced pressure
5. 5
   OtherThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:4)

Procedure

A solution of (5R)-5-[(E)-2-(5-amino-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (198 mg) in trifluoroacetic acid (4 mL) and anisole (2 mL) was stirred at 80° C. for six hours. Saturated aqueous sodium bicarbonate was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:4) to give (5R)-5-[(E)-2-(5-amino-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one as a light brown solid (61 mg, 44%).

Source