p-Anisoyl chloride → HCID 21084206, compound

HRID 347809Notes

Reaction equation

HRID 347809 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[NH:2]2.C(N(CC)CC)C.[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>C(Cl)(Cl)Cl>[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([N:2]2[CH:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:4]3[CH2:7][CH:1]2[CH2:6][CH2:5]3)=[O:27])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 13258847Ethyl 2-azabicyclo[2.2.1]heptane-3-carboxylate

Product 1

HCID 21084206HCID 21084206, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl 2-azabicyclo[2.2.1]heptane-3-carboxylate (181 mg, 1.07 mmol) obtained in Example 1 (b) in chloroform (2 ml) were added triethylamine (0.16 ml, 1.18 mmol) and 4-methoxybenzoyl chloride (201 mg, 1.18 mmol) while being cooled with ice. After a reaction at room temperature for 1 hour, the reaction mixture was washed with 1N hydrochloric acid, saturated sodium bicarbonate water and saturated brine successively, and dried over magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (25%–40% ethyl acetate/hexane), to give ethyl 2-(4-methoxybenzoyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate (239 mg, 74%).

Workup

  1. temperaturewhile being cooled with ice
  2. customAfter a reaction at room temperature for 1 hour
  3. washthe reaction mixture was washed with 1N hydrochloric acid, saturated sodium bicarbonate water and saturated brine successively
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (25%–40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-584d4e11e55b4d63b9352f93bec07687
Source dataset
uspto-grants-2007_02
Patent number
US07176217B2

Reaction notes

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