Reaction #1909783

Reaction equation

1-tert-butoxycarbonyl-4-ethylisonipecotic acid ethyl ester

lithium hydroxide

→

title compound

Yield 45.3%

1-tert-Butoxycarbonyl-4-ethylisonipecotic acid

Yield 45.3%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturethe mixture was refluxed
2. 2
   Temperatureunder heating for 20 hours
3. 3
   ConcentrationThen, the reaction mixture was concentrated
4. 4
   workup.ADDITIONwater was added to the residue
5. 5
   WashThe aqueous layer was washed with ether
6. 6
   Extractionextracted with ether
7. 7
   DryingThe organic layer was dried over anhydrous magnesium sulfate
8. 8
   Concentrationconcentrated under reduced pressure

Procedure

To a solution of 1-tert-butoxycarbonyl-4-ethylisonipecotic acid ethyl ester (570 mg) in ethanol (10 ml) was added a 1M lithium hydroxide solution (8 ml), and the mixture was refluxed under heating for 20 hours. Then, the reaction mixture was concentrated, and water was added to the residue. The aqueous layer was washed with ether acidified with 1N hydrochloric acid, and extracted with ether. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (233 mg, yield 45%).

Source