1,1'-Carbonyldiimidazole → HCID 44192926, compound

HRID 2194361Notes

Reaction equation

HRID 2194361 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[O:4][N:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:22]1[NH:27][CH2:26][CH2:25][N:24]2[C:28](=[O:31])[CH2:29][CH2:30][C@@H:23]12>CC#N>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([N:27]2[CH2:26][CH2:25][N:24]3[C:28](=[O:31])[CH2:29][CH2:30][C@H:23]3[CH2:22]2)=[O:9])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 8530853-Methylisoxazole-5-carboxylic acidHCID 18439805(S)-Hexahydropyrrolo[1,2-A]pyrazin-6(2H)-one

Product 1

HCID 44192926HCID 44192926, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 3-methyl-isoxazole-5-carboxylic acid (100 mg, 0.79 mmol) in CH3CN (10 ml), carbonyldiimidazole (140 mg, 0.87 mmol) was added at room temperature. After stirring for 1 hour, a solution of (S)-(−)-hexahydropyrrolo[1,2-a]pyrazin-6(7H)-one (compound of Description 5, 121 mg, 0.86 mmol) in CH3CN (2 ml), was added dropwise at room temperature. After stirring the solution for 20 hours, the solvent was removed under vacuum and the residue purified by flash chromatography (DCM/MeOH 95/5 respectively) to afford the title compound as an oil (160 mg, 82% yield).

Workup

  1. stirringAfter stirring the solution for 20 hours
  2. customthe solvent was removed under vacuum
  3. customthe residue purified by flash chromatography (DCM/MeOH 95/5 respectively)

Sources & evidence

ORD record
ord-c6d9824bad5a43c4a6fc8ffc69262449
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

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