Tert-Butylamine → N-t-butyl-4,4-diphenyl-2-cyclopentenylamine

Participants

Reaction Steps

To a solution of 4,4-diphenyl-2-cyclopenten-1-one (0.40 g), t-butylamine (0.75 g) in methylene chloride (9 ml) was added dropwise a solution of titanium tetrachloride (0.50 g) in methylene chloride (5 ml) at -70° C. to -60° C. After being stirred for 2 hours, sodium borohydride (0.35 g) and methanol (6 ml) were added successively at 0° C. After being stirred for 0.5 hour, the precipitate was filtered off using celite and the filtrate was condensed under reduced pressure. To the residue, 1N sodium hydroxide aqueous solution was added and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol as an eluent to give N-t-butyl-4,4-diphenyl-2-cyclopentenylamine (0.13 g) and N-t-butyl-3,3-diphenylcyclopentylamine (0.19 g) respectively.

Provenance & Evidence