Reaction #1121802

Reaction equation

1-benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate

LiOH

→

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

Yield 93.8%

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

To 1-benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate (3.0 g, 10.0 mmol) in ethanol (15 mL) was added LiOH (15.0 mL, 30.1 mmol), and the reaction mixture was stirred at 86° C. 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), and washed with brine and dried over sodium sulfate. After removal of the solvent, 1-(benzyloxycarbonyl)-3-methylpiperidine-3-carboxylic acid (2.6 g, 92% yield) was isolated as an oil.

Source