Binap, (A+-)- → tert-Butyl (1S,4S)-5-(2-methyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

3-Bromo-2-methylpyridine (258 mg, 1.5 mmol), tert-butyl (1S,4S)-3,6-diazabicyclo[2.2.1]heptane-3-carboxylate (397 mg, 2 mmol), Pd2(DBA)3 (30 mg, 0.033 mmol), sodium tert-butoxide (160 mg, 1.66 mmol), BINAP (60 mg, 0.096 mmol) were placed in anhydrous THF (5 ml), purged with argon and heated under microwave heating at 80° C. in a closed vial for 40 minutes. The mixture was filtered through kieselguhr, concentrated under reduced pressure and purified by column chromatography (silica, gradient from 0 to 50% ethyl acetate in DCM) to yield 230 mg of an orange solid (0.80 mmol, yield 53%). MS (ESI) m/z=290.1 [M+1]+.

Provenance & Evidence