AL-1095 explained

AL-1095,^[1] is a centrally acting stimulant drug with comparable effects to amphetamine,^[2] developed by Bristol in the 1970s.^[3]

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.

See also

• Butyltolylquinuclidine
• Desoxypipradrol
• SCH-5472

Notes and References

1. US . 3506673 . 2-(4'Halo)-Benzhydryl-3-Quinuclidinols . 14 April 1970 . Warawa ED, Mueller NJ . Aldrich Chemical Company .
2. Book: Hedblom P, Grinspoon L . The Speed Culture: Amphetamine Use and Abuse in America . Harvard University Press . Cambridge . 1975 . 50 . 0-674-83192-6 . registration .
3. Warawa EJ, Mueller NJ . Quinuclidine Chemistry. 3. β-cis-2-(4'-Chlorobenzhydryl)-3-quinuclidinol, a New Central Nervous System Stimulant. Importance of the Benzhydryl Configuration . Journal of Medicinal Chemistry . 18 . 1 . 71–4 . January 1975 . 803245 . 10.1021/jm00235a016 .