(3R)-3-Ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-one → (S)-6-Fluoro-3-methyl-3,4-dihydroquinoxalin-2(1H)-one

HRID 898253Notes

Reaction equation

HRID 898253 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-])=O)=[C:6]([NH:8][C@H:9]([C:11](O)=[O:12])[CH3:10])[CH:7]=1.C([C@H]1NC2C(=CC(F)=CC=2)NC1=O)C>>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:14][C:11](=[O:12])[C@H:9]([CH3:10])[NH:8]2

Participants

3

Reactant 2

HCID 69220784(3R)-3-Ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-oneHCID 69223262N-(5-fluoro-2-nitrophenyl)-L-alanine

Product 1

HCID 69221304(S)-6-Fluoro-3-methyl-3,4-dihydroquinoxalin-2(1H)-one

Procedure

N-(5-Fluoro-2-nitrophenyl)-L-alanine was treated according to the procedure for the preparation of (3R)-3-ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-one (see Example 1) to yield (3S)-6-fluoro-3-methyl-3,4-dihydroquinoxalin-2(1H)-one. MS (ESI) m/z 181 ([M+H]+); Anal. Calcd for C9H9FN2O: C, 59.99; H, 5.03; N, 15.55. Found: C, 59.89; H, 4.88; N, 15.46.

Sources & evidence

ORD record
ord-ce1ebdbc7db04bf28aa7a39c4a3aba32
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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