Cesium carbonate → Methyl cis(+/-)-3-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methoxybenzoate

HRID 43962Notes

Reaction equation

HRID 43962 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:14][O:15][C@H:16]1[C@@H:21]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:20][CH2:19][NH:18][CH2:17]1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH2:25]([O:24][C:23]([NH:22][C@H:21]1[CH2:20][CH2:19][N:18]([C:2]2[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:17][C@H:16]1[O:15][CH3:14])=[O:32])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 15618226Methyl 3-bromo-5-methoxybenzoateHCID 86648490Benzyl cis(+/-)-[3-methoxypiperidin-4-yl]carbamate

Product 1

HCID 86648844Methyl cis(+/-)-3-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methoxybenzoateYield 27.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

The same operation as in Example (42a) was performed using methyl 3-bromo-5-methoxybenzoate obtained in Example (257a) (371 mg, 1.51 mmol), benzyl cis(±)-(3-methoxypiperidin-4-yl)-carbamate obtained in Example (40b) (400 mg, 1.51 mmol), palladium acetate (34 mg, 0.15 mmol), (±)-BINAP (188 mg, 0.30 mmol), cesium carbonate (1.08 g, 3.33 mmol), 1,4-dioxane (15 mL) and DMF (4.5 mL), to obtain 178 mg of the title compound as a yellow oily substance (27%).

Sources & evidence

ORD record
ord-a8d4791c8dcd493a80b69a4cdeb87a9e
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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