[3,3-dimethyl-1(S)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butyl]carbamic acid benzyl ester → 3,3-dimethyl-1(S)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butylamine

Participants

Reaction Steps

[3,3-Dimethyl-1(S)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butyl]carbamic acid benzyl ester (15 g) was dissolved in ethyl acetate (300 ml) and after degassing with nitrogen, 10% Pd—C (1.5 g) was added under nitrogen atmosphere. The reaction mixture was hydrogenated at 50 psi for 4 h. The solution was filtered through celite and washed with EtOAc. The solvent was removed to give 3,3-dimethyl-1(S)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butylamine (8 g) as a white solid.

Provenance & Evidence