(1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane
The present invention discloses (1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane, salts thereof, and its use to treat pain and other disorders associated with the nicotinic acetylcholine receptor.
1. A process for preparing compound (5J),
comprising the steps of:
a) treating compound (5D),
with an aqueous acid;
b) treating the mixture from step (a) with a compound of formula (A),
wherein R z is phenyl optionally substituted with alkyl, alkoxy or halo in the presence of magnesium bromide in a mixture of isopropyl alcohol and dichloromethane to provide a compound of formula (B),
c) using the compound of formula (B) to preparing the compound (5J).
2. The process of claim 1 , wherein compound (5J) is prepared from the compound of formula (B) by a process comprising the steps of:
a) treating the compound of formula (B) with a reagent that will convert the hydroxyl group into a leaving group;
b) treating the compound from step (a) with potassium tert-butoxide under heated conditions;
c) treating the compound from step (b) with an aqueous acid to obtain a pH<1 followed by adjusting the pH to 4-5 to provide compound (5H),
d) using compound (5H) to prepare compound (5J).