Hydrogen Bromide → Ethyl 6-(bromoacetyl)-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate
Reaction equation
[C:1]([C:4]1[N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[C:12](=[O:13])[C:7]2=[C:6]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:3])[CH3:2].[Br:28]Br.Br.C(=O)(O)[O-].[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl>[Br:28][CH2:2][C:1]([C:4]1[N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[C:12](=[O:13])[C:7]2=[C:6]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:5]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:3]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of ethyl 6-acetyl-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate (0.50 g, 1.35 mmol; Example 7, step 7), bromine (0.24 g, 1.49 mmol), 33% hydrobromide in glacial acetic acid (10 drops) in chloroform (15 mL) was stirred at room temperature for 6 hours. The mixture was treated with aqueous sodium bicarbonate and diluted with chloroform. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 20 to 80% ethyl acetate in hexane to afford the title compound. ES MS M+1=407, 409
Workup
- extractionThe organic extract
- dry with materialwas dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-52b042cee15f4db18ccbe04c938009d0
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538112B2
Reaction notes
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