Pyridine → HCID 11149704, compound

HRID 347724Notes

Reaction equation

HRID 347724 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][CH3:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 70770Ethyl 4-piperidinecarboxylateHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 11149704HCID 11149704, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-piperidinecarboxylic acid ethyl ester (5.0 g) and 2-methoxyphenylboronic acid (5.0 g) in dichloromethane (100 ml) are added pyridine (12.9 ml), anhydrous copper (II) acetate (5.78 g) and Molecular sieves 4 Å (100 g), and the mixture is stirred at 25° C. for 2 days. The reaction solution is filtered, and the filtrate is poured into 10% aqueous citric acid solution, and the organic layer is washed successively with aqueous sodium hydrogen carbonate solution, and saturated brine. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: gradient, 0% to 100% hexane/ethyl acetate) to give the title compound.

Workup

  1. filtrationThe reaction solution is filtered
  2. additionthe filtrate is poured into 10% aqueous citric acid solution
  3. washthe organic layer is washed successively with aqueous sodium hydrogen carbonate solution, and saturated brine
  4. customThe solvent is evaporated under reduced pressure
  5. customthe residue is purified by silica gel column chromatography (eluent: gradient, 0% to 100% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9a5b3f2869fb48c9b460b95a0cbe92f3
Source dataset
uspto-grants-2007_02
Patent number
US07176199B2

Reaction notes

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