反应详情

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.

1. concentrationwas concentrated in vacuo to a volume of about 50 ml
2. custompartitioned between 100 ml of ether and 300 ml of H2O
3. additionAfter addition of about 2 ml of TEA the aqueous layer
4. washwas washed with ether (3×)
5. washeach ether in turn washed with H2O