Eslicarbazepine acetate → Oxcarbazepine

HRID 526675Notes

Reaction equation

C([O:4][C@@H:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:16]([NH2:18])=[O:17])[C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]=2[CH2:6]1)(=O)C.C(O[C@H]1C2C=CC=CC=2N(C(N)=O)C2C=CC=CC=2C1)(=O)C.O[C@@H]1C2C=CC=CC=2N(C(N)=O)C2C=CC=CC=2C1.O[C@H]1C2C=CC=CC=2N(C(N)=O)C2C=CC=CC=2C1>>[O:4]=[C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:16]([NH2:18])=[O:17])[C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]=2[CH2:6]1

Participants

Reactant 4

HCID 179344Eslicarbazepine acetate

HCID 9816485R-Licarbazepine

HCID 9881504Eslicarbazepine

HCID 10590023(R)-Licarbazepine Acetate

Product 1

HCID 34312Oxcarbazepine

Procedure

In an another embodiment, the invention provides a process for preparing (S)-(−)-10-acetoxy-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide, or (R)-(+)-10-acetoxy-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide from (S)-(+)-10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide or (R)-(−)-10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide, which are obtained by enantioselective reduction of 10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxamide or derivatives thereof in presence of sodium borohydride and tartaric acid derived ester of phenyl boronic acid.

Workup

customIn an another embodiment, the invention provides a process

Sources & evidence

ORD record: ord-cccd5c10a81849f785ce907280cce3f6
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346760B2

Reaction notes

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