2-Benzylidene-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acid → Mitiglinide

HRID 2261531Notes

Reaction equation

HRID 2261531 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]=1

Participants

3

Reactant 1

HCID 545718482-Benzylidene-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acid

Product 1

HCID 121891Mitiglinide

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

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
ord-9201c5aab8724614baca1a7ac8920d1a
Source dataset
uspto-grants-2010_12
Patent number
US07847107B2

Reaction notes

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