Potassium Bromide → 8-bromo-5-cyclopropyl-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one
Reaction equation
B1([O-])OO1.O.O.O.O.[Na+].[K+].[Br-:11].[CH:12]1([N:15]2[C:22](=[O:23])[CH2:21][CH2:20][NH:19][C:18]3[CH:24]=[CH:25][CH:26]=[CH:27][C:17]=3[CH2:16]2)[CH2:14][CH2:13]1>C(O)(=O)C.[NH4+].[NH4+].O.O.O.O.[O-][Mo]([O-])(=O)=O>[Br:11][C:26]1[CH:25]=[CH:24][C:18]2[NH:19][CH2:20][CH2:21][C:22](=[O:23])[N:15]([CH:12]3[CH2:14][CH2:13]3)[CH2:16][C:17]=2[CH:27]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Sodium perborate tetrahydrate (1.07 g, 6.94 mmol) was added in one portion to a suspension of KBr (0.770 g, 6.47 mmol), 5-cyclopropyl-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one (1.00 g, 4.62 mmol) and ammonium molybdate tetrahydrate (0.114 mg, 0.092 mmol) in acetic acid (10 ml). The mixture was stirred at room temperature for 24 hours, then quenched with sodium carbonate (aqueous saturated) and a few drops of NaOH (10% aqueous). The mixture was extracted with ethyl acetate and the combined organic phases were washed with sodium carbonate, dried over sodium sulfate filtered and concentrated. Purification of the crude mixture by silica gel flash chromatography (0-20% methanol in ethyl acetate) gave the desired product as a brown solid (0.619 g, 45%).
Workup
- customquenched with sodium carbonate (aqueous saturated) and a few drops of NaOH (10% aqueous)
- extractionThe mixture was extracted with ethyl acetate
- washthe combined organic phases were washed with sodium carbonate
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customPurification of the crude mixture by silica gel flash chromatography (0-20% methanol in ethyl acetate)
Sources & evidence
- ORD record
- ord-9f1ec2078da144db96fefe9a90d4b4e7
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765728B2
Reaction notes
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