Potassium Carbonate → HCID 86646769, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:14][C@@H:13]3[C@H:9]2[CH2:10][NH:11][CH2:12]3)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:22]([CH3:28])([CH3:27])[C:23]([O:25][CH3:26])=[O:24]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:14][C@@H:13]3[C@H:9]2[CH2:10][N:11]([C:22]([CH3:28])([CH3:27])[C:23]([O:25][CH3:26])=[O:24])[CH2:12]3)=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of (1R*,5S*,6R*)-6-(4-chlorophenyl)-3-azabicyclo[3.2.0]heptane (Steiner, G., et al., Heterocycles, 1995, 40, 319-330) (1.0 g, 1.3 mmol) in N,N-dimethylformamide (40 mL) were added potassium carbonate (1.0 g, 7.5 mmol) and methyl 2-bromo-2-methylpropanoate (0.4 mL, 3.0 mmol, Aldrich). After stirring at 80° C. for 16 hours, the reaction mixture was cooled and quenched with water (30 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was then purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% of ethyl acetate in hexanes) to obtain the titled compound. MS (ESI+) m/z 308 (M+H)+.
Workup
- temperaturethe reaction mixture was cooled
- customquenched with water (30 mL)
- extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
- dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was then purified by column chromatography
Sources & evidence
- ORD record
- ord-b5d2cac56229466191a1953f18eef9d3
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507493B2
Reaction notes
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