3-(3-Fluoro-4-methoxybenzoyl)propionic acid → 1-(3-Fluoro-4-methoxyphenyl)-4-((R)-octahydropyrido[1,2-a]pyrazin-2-yl)butane-1,4-dione

HRID 456418Notes

Reaction equation

HRID 456418 reaction equation
COC1C=C([C:11](=O)[CH2:12][CH2:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]3CCC[C@H:18]3[CH2:17]2)=O)C=CC=1OC.C(OC(N1CCCC[C@@H]1C(O)=O)=O)(C)(C)C.[F:42][C:43]1[CH:44]=[C:45]([CH:53]=[CH:54][C:55]=1[O:56][CH3:57])[C:46]([CH2:48][CH2:49][C:50]([OH:52])=O)=[O:47]>>[F:42][C:43]1[CH:44]=[C:45]([C:46](=[O:47])[CH2:48][CH2:49][C:50]([N:19]2[CH2:20][CH2:21][N:16]3[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:17]3[CH2:18]2)=[O:52])[CH:53]=[CH:54][C:55]=1[O:56][CH3:57]

Participants

4

Reactant 3

HCID 676713-(3-Fluoro-4-methoxybenzoyl)propionic acidHCID 688618(2R)-1-[(tert-butoxy)carbonyl]piperidine-2-carboxylic acidHCID 248863341-(3,4-Dimethoxyphenyl)-4-((S)-hexahydropyrrolo[1,2-a]pyrazin-2-yl)butane-1,4-dione

Product 1

HCID 248865711-(3-Fluoro-4-methoxyphenyl)-4-((R)-octahydropyrido[1,2-a]pyrazin-2-yl)butane-1,4-dione

Procedure

93 mg of the title compound were prepared as described for 1-(3,4-dimethoxyphenyl)-4-((S)-hexahydropyrrolo[1,2-a]pyrazin-2-yl)butane-1,4-dione, using (R)-1-(tert-butoxycarbonyl)piperidine 2 carboxylic acid instead of BOC-protected proline and 3-(3-fluoro-4-methoxybenzoyl)propionic acid instead of 3-(3,4-dimethoxybenzoyl)propionic acid.

Sources & evidence

ORD record
ord-ebce91a0bdcf4747af517199af5f5467
Source dataset
uspto-grants-2007_03
Patent number
US07186721B2

Reaction notes

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