Cesium carbonate → Methyl-3-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzoate
Reaction equation
CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:41]1[O:50][C:44]2([CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[O:43][CH2:42]1.[CH3:51][O:52][C:53](=[O:61])[C:54]1[CH:59]=[CH:58][CH:57]=[C:56](Br)[CH:55]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(O)(C)C>[CH3:51][O:52][C:53](=[O:61])[C:54]1[CH:59]=[CH:58][CH:57]=[C:56]([N:47]2[CH2:48][CH2:49][C:44]3([O:50][CH2:41][CH2:42][O:43]3)[CH2:45][CH2:46]2)[CH:55]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 120 °C
Procedure
Procedure adopted from Tetrahedron Lett., 2007, 48, 2519. A thick-walled glass reaction vessel was charged with palladium(II)acetate (235 mg, 1.05 mmol), X-Phos (500 mg, 1.05 mmol, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl), cesium carbonate (6.82 g, 20.95 mmol) and 5:1 (v/v) toluene:t-BuOH (20 mL). The stirred contents were purged with nitrogen and a solution of 4-piperidone ethylene ketal (2.70 mL, 20.95 mmol) and methyl-3-bromobenzoate (4.95 g, 23.02 mmol) in 5:1 (v/v) toluene:t-BuOH (100 mL) was added. After stirring for 2 minutes, the vessel was sealed and the reaction mixture was heated at 120° C. for 16 hours. Upon cooling to room temperature, the reaction mixture was filtered through celite and the filtrate was concentrated.
Workup
- customA thick-walled glass reaction vessel
- customThe stirred contents were purged with nitrogen
- customthe vessel was sealed
- temperatureUpon cooling to room temperature
- filtrationthe reaction mixture was filtered through celite
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-d3973b10688b4c2a97a5e2ce273c5f9b
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388176B2
Reaction notes
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