Reaction #452456

Reaction equation

BOC-ON

4-carboxybicyclo[2.2.2]octanemethylamine hydrochloride salt

H2O

→

title compound

Boc-4-aminomethylbicyclo-[2.2.2]octane carboxylic acid

Solvents

THF

Conditions

Workup

1. 1
   Concentrationwas concentrated in vacuo to a volume of about 50 ml
2. 2
   Otherpartitioned between 100 ml of ether and 300 ml of H2O
3. 3
   workup.ADDITIONAfter addition of about 2 ml of TEA the aqueous layer
4. 4
   Washwas washed with ether (3×)
5. 5
   Washeach ether in turn washed with H2O

Procedure

A sample of 8.79 g (40.0 mmol) of 4-carboxybicyclo[2.2.2]octanemethylamine hydrochloride salt suspended in 100 ml each of THF and H2O was treated with 20.0 ml (14.6 g=3.3 equiv.) of TEA, followed by 11.8 g (47.9 mmol) of BOC-ON reagent. All went into solution, and after stirring 24 hr the solution was concentrated in vacuo to a volume of about 50 ml and partitioned between 100 ml of ether and 300 ml of H2O. After addition of about 2 ml of TEA the aqueous layer was washed with ether (3×), each ether in turn washed with H2O, and the combined aqueous layer was acidified with 5% KHSO4 to give the title compound as a white solid, isolated by filtration and drying in vacuo.

Source