2-Benzylidene-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acid → Mitiglinide
Reaction equation
[CH:1](=[C:8]([CH2:12][C:13]([N:15]1[CH2:23][C@H:22]2[C@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:16]1)=[O:14])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Rh]>[CH:5]1[CH:4]=[CH:3][C:2]([CH2:1][C@H:8]([C:9]([OH:11])=[O:10])[CH2:12][C:13]([N:15]2[CH2:16][C@H:17]3[C@H:22]([CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:23]2)=[O:14])=[CH:7][CH:6]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
The preparation was carried out in the same manner as in Example 1, except that 10.04 mg of PCPPM was used instead of 3.02 mg of PCPPM of Example 1, and 328 mg of CATAXA/rhodium-1,5-cyclooctadiene complex (S/C=3,000), which is an immobilized rhodium, was used instead of 1.18 mg of rhodium-1,5-cyclooctadiene-chloride complex of Example 1. After the reaction, 2-benzylidene-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acid was not detected, and the optical purity of mitiglinide thus obtained was 95.5% e.e.
Sources & evidence
- ORD record