4-Cyanophenylboronic acid → Racemic 4-[7-hydroxy-6,6-dimethyl-5,7-dihydrocyclopenta[c]pyridin-4-yl]benzonitrile
Reaction equation
Br[C:2]1[C:3]2[CH2:10][C:9]([CH3:12])([CH3:11])[CH:8]([OH:13])[C:4]=2[CH:5]=[N:6][CH:7]=1.[C:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)#[N:15]>>[OH:13][CH:8]1[C:4]2[CH:5]=[N:6][CH:7]=[C:2]([C:19]3[CH:20]=[CH:21][C:16]([C:14]#[N:15])=[CH:17][CH:18]=3)[C:3]=2[CH2:10][C:9]1([CH3:12])[CH3:11]Participants
3
Procedure
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+).
Sources & evidence
- ORD record
- ord-66b62eae71874ff9894fbc57ac429e22
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187429B2
Reaction notes
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