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

HRID 2261530Notes

Reaction equation

HRID 2261530 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].C1CCC=CCCC=1.F[B-](F)(F)F.[H+]>[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 86627670Rhodium 1,5-cyclooctadiene tetrafluoroboric acidCatalyst

Procedure

The preparation was carried out in the same manner as in Example 1, except that 1.94 mg of rhodium-1,5-cyclooctadiene-tetrafluoroboric acid complex hydrate (S/C=10000) was used instead of 1.18 mg of rhodium-1,5-cyclooctadiene-chloride complex of Example 1. After the reaction, the residual ratio of 2-benzylidene-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acid was 2.21%, and the optical purity of mitiglinide thus obtained was 95.9% e.e.

Workup

  1. customAfter the reaction

Sources & evidence

ORD record
ord-1ce2321499f942848e1c62d4f27c2c00
Source dataset
uspto-grants-2010_12
Patent number
US07847107B2

Reaction notes

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