Benzyl Bromide → Ethyl 2-benzyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate

HRID 1842454Notes

Reaction equation

[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=[C:3]12.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C>[CH2:22]([N:7]1[CH2:6][CH2:5][N:4]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=[C:3]2[C:2]1=[O:1])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a vial charged with ethyl 1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate (0.0298 g, 0.143 mmol) was added cesium carbonate (0.061 g, 0.186 mmol), benzyl bromide (0.037 g, 0.2145 mmol), and acetonitrile (1 mL). The vial was capped and was shaken at 70° C. overnight. The solids were removed by filtration and the solution was concentrated to give crude ethyl 2-benzyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate Intermediate 12.

Workup

customThe vial was capped
customThe solids were removed by filtration
concentrationthe solution was concentrated

Sources & evidence

ORD record: ord-09721c52c99344b9ba194647a3604d93
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946223B2

Reaction notes

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