(2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine → Mitiglinide

HRID 2261533Notes

Reaction equation

HRID 2261533 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]=1

Participants

3

Reactant 2

HCID 10209545(2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidineHCID 545718482-Benzylidene-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acid

Product 1

HCID 121891Mitiglinide

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

  1. customAfter the reaction

Sources & evidence

ORD record
ord-bb6f6adbe4b0476c81f9ff7f69d2ea12
Source dataset
uspto-grants-2010_12
Patent number
US07847107B2

Reaction notes

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