3-Fluoro-4-trifluoromethyl-phenylboronic acid → Racemic 4-[3-fluoro-4-(trifluoromethyl)phenyl]-6,6-dimethyl-5,7-dihydrocyclopenta[c]pyridin-7-ol

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Reaction Steps

In analogy to the procedure described for the preparation of examples 85 and 86, 4-bromo-6,6-dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridin-7-ol (intermediate A-17) and 3-fluoro-4-trifluoromethyl-phenylboronic acid gave racemic 4-[3-fluoro-4-(trifluoromethyl)phenyl]-6,6-dimethyl-5,7-dihydrocyclopenta[c]pyridin-7-ol. SFC separation afforded (+)-(7R)-4-[3-fluoro-4-(trifluoromethyl)phenyl]-6,6-dimethyl-5,7-dihydrocyclopenta[c]pyridin-7-ol (example 108) and (−)-(7S)-4-[3-fluoro-4-(trifluoromethyl)phenyl]-6,6-dimethyl-5,7-dihydrocyclopenta[c]-pyridin-7-ol (example 109) as white solids. MS: 309.0 (M+H+).

Provenance & Evidence