AL-1095

AL-1095, is a centrally acting stimulant drug with comparable effects to amphetamine, developed by Bristol in the 1970s.

Synthesis


The first-step is a mixed-aldol condensation between 3-quinuclidinone [3731-38-2] (1) and benzaldehyde (2) gives 2-benzylidene-3-oxoquinuclidine [24123-89-5] (3). The conjugate addition of the Grignard reagent formed from 4-bromochlorobenzene [106-39-8] (4) to the enone gives the benzhydryl (5). MPV reduction of the carbonyl gives the syn stereoisomers, whereas borohydride gave trans. Both diastereoisomers are active but in only one of the enantiomers.