Reaction #452459

Reaction equation

product

Boc-4-aminomethylbicyclo-[2.2.2]octane nitrile

→

Boc-4-aminomethylbicyclo-[2.2.2]octane methylamine

Solvents

CH3OH

HOAc

H2O

Conditions

Workup

1. 1
   OtherThe catalyst was removed by filtration through Celite
2. 2
   Concentrationthe filtrate was concentrated in vacuo to an oily residue, which
3. 3
   Otherwas flushed/evaporated with CH3OH (1×) and CH2Cl2 (2×)
4. 4
   Otherto crystallize toward the end of the evaporation, and ether (up to 300 ml)
5. 5
   workup.ADDITIONwas added
6. 6
   Otherthe precipitation
7. 7
   OtherThe white solid was triturated
8. 8
   Otherisolated by filtration
9. 9
   Washwashing with ether
10. 10
    Otherto give
11. 11
    Otherafter drying in vacuo

Procedure

A solution of 6.75 g (25.5 mmol) of the product from step D in 200 ml of CH3OH plus 4 ml of HOAc and 2 ml of H2O was hydrogenated over 1.63 g of PtO2 in a Parr shaker at 55 psi for 22 hr. The catalyst was removed by filtration through Celite, and the filtrate was concentrated in vacuo to an oily residue, which was flushed/evaporated with CH3OH (1×) and CH2Cl2 (2×). Product began to crystallize toward the end of the evaporation, and ether (up to 300 ml) was added to complete the precipitation. The white solid was triturated and isolated by filtration and washing with ether to give, after drying in vacuo, the title compound as the acetate salt.

Source