Reaction #1121805

Reaction equation

LiOH

1-benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate

→

1-(benzyloxycarbonyl)-3-methylpyrrolidine-3-carboxylic acid

Yield 99.1%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherThe ethanol was removed
2. 2
   workup.ADDITIONether (30 mL) was added
3. 3
   OtherThe aqueous layer was separated
4. 4
   Extractionextracted with ethyl acetate (50 mL)
5. 5
   Washwashed with brine
6. 6
   Dryingdried over sodium sulfate
7. 7
   OtherAfter removal of the solvent

Procedure

A 3M LiOH solution (14.7 mL, 29.4 mmol) was added to 1-benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate (2.72 g, 9.81 mmol) in ethanol (15 mL), and the reaction mixture was stirred at 78° C. (bath) for 1 hour. The ethanol was removed, and ether (30 mL) was added. The aqueous layer was separated and acidified with saturated potassium hydrogen sulfate to a pH of about 3 to about 4, extracted with ethyl acetate (50 mL), washed with brine and dried over sodium sulfate. After removal of the solvent, 1-(benzyloxycarbonyl)-3-methylpyrrolidine-3-carboxylic acid (2.56 g, 99% yield) was isolated as an oil.

Source