3-Bromo-2-oxobornane-10-sulphonic acid → HCID 131724587, compound
Reaction equation
[Br:1][CH:2]1[CH:7]2[C:8]([CH3:10])([CH3:9])[C:4]([CH2:11][S:12]([OH:15])(=[O:14])=[O:13])([CH2:5][CH2:6]2)[C:3]1=[O:16].[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C:25]([OH:41])([C:32]([C:34]1[CH:39]=[CH:38][C:37]([I:40])=[CH:36][CH:35]=1)=[CH2:33])[CH2:26][N:27]1[CH:31]=[N:30][CH:29]=[N:28]1>>[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C@:25]([OH:41])([C:32]([C:34]1[CH:35]=[CH:36][C:37]([I:40])=[CH:38][CH:39]=1)=[CH2:33])[CH2:26][N:27]1[CH:31]=[N:30][CH:29]=[N:28]1.[Br:1][CH:2]1[CH:7]2[C:8]([CH3:10])([CH3:9])[C:4]([CH2:11][S:12]([O-:15])(=[O:14])=[O:13])([CH2:5][CH2:6]2)[C:3]1=[O:16]Participants
3
Procedure
A solution of (+)-3-bromocamphor-10-sulphonic acid (36.3 g, 0.110 moles) in IMS (40 ml) was added to a solution of the product of step (f) (50 g, 0.110 moles) in IMS (300 ml). After seeding, the resulting slurry was granulated for 20 hours at room temperature. A white solid (22 g, 0.03 moles) was collected by filtration after further granulating for 1 hour at low temperature. The chiral purity was assessed as 95% ee by chiral HPLC using a Chiralcel™ OD column and eluting with ethanol/hexane [40:60].
Workup
- washeluting with ethanol/hexane [40:60]