3-(4-Chlorobenzoyl)propionic acid → 1-(4-Chlorophenyl)-4-(octahydropyrido[1,2-a]pyrazin-2-yl)butane-1,4-dione

HRID 456414Notes

Reaction equation

HRID 456414 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(N1CCCCC1C(O)=O)=O)(C)(C)C.[Cl:42][C:43]1[CH:55]=[CH:54][C:46]([C:47]([CH2:49][CH2:50][C:51]([OH:53])=O)=[O:48])=[CH:45][CH:44]=1>>[Cl:42][C:43]1[CH:44]=[CH:45][C:46]([C:47](=[O:48])[CH2:49][CH2:50][C:51]([N:19]2[CH2:20][CH2:21][N:16]3[CH2:14][CH2:13][CH2:12][CH2:11][CH:17]3[CH2:18]2)=[O:53])=[CH:54][CH:55]=1

Participants

4

Reactant 3

HCID 776043-(4-Chlorobenzoyl)propionic acidHCID 5818311-[(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 223931421-(4-Chlorophenyl)-4-(octahydropyrido[1,2-a]pyrazin-2-yl)butane-1,4-dione

Procedure

463 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 1-(tert-butoxycarbonyl)piperidine 2 carboxylic acid instead of BOC-protected proline and 3-(4-chlorobenzoyl)propanoic acid instead of 3-(3,4-dimethoxybenzoyl)propionic acid.

Sources & evidence

ORD record
ord-468f711ebefe45929981b77c5947b146
Source dataset
uspto-grants-2007_03
Patent number
US07186721B2

Reaction notes

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