(2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine → Mitiglinide
Reaction equation
CC(OC(N1[C@H](CP(C2C=CC=CC=2)C2C=CC=CC=2)C[C@H](P(C2C=CC=CC=2)C2C=CC=CC=2)C1)=O)(C)C.[CH:40](=[C:47]([CH2:51][C:52]([N:54]1[CH2:62][C@H:61]2[C@H:56]([CH2:57][CH2:58][CH2:59][CH2:60]2)[CH2:55]1)=[O:53])[C:48]([OH:50])=[O:49])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[CH:44]1[CH:43]=[CH:42][C:41]([CH2:40][C@H:47]([C:48]([OH:50])=[O:49])[CH2:51][C:52]([N:54]2[CH2:55][C@H:56]3[C@H:61]([CH2:60][CH2:59][CH2:58][CH2:57]3)[CH2:62]2)=[O:53])=[CH:46][CH:45]=1Participants
3
Procedure
The preparation was carried out in the same manner as in Example 1, except that 2.92 mg of BPPM was used instead of 3.02 mg of PCPPM of Example 1. After the reaction, the residual ratio of 2-benzylidene-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acid was 10.85%, and the optical purity of mitiglinide thus obtained was 96.1% e.e.
Workup
- customAfter the reaction