4-Cyanophenylboronic acid → Racemic 4-[7-hydroxy-6,6-dimethyl-5,7-dihydrocyclopenta[c]pyridin-4-yl]benzonitrile

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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 4-cyanophenylboronic acid gave racemic 4-[7-hydroxy-6,6-dimethyl-5,7-dihydrocyclopenta[c]pyridin-4-yl]benzonitrile. SFC separation afforded (+)-4-[(7R or 7S)-7-hydroxy-6,6-dimethyl-5,7-dihydrocyclopenta[c]pyridin-4-yl]benzonitrile (example 87) and (−)-4-[(7S or 7R)-7-hydroxy-6,6-dimethyl-5,7-dihydrocyclopenta[c]pyridin-4-yl]benzonitrile (example 88) as white solids. MS: 264.9 (M+H+).

Provenance & Evidence