4-Methoxybenzenesulfonyl chloride → HCID 15529569, compound

HRID 347798Notes

Reaction equation

HRID 347798 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:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>C(Cl)(Cl)Cl>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([S:28]([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:30])=[O:29])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 13258847Ethyl 2-azabicyclo[2.2.1]heptane-3-carboxylate

Product 1

HCID 15529569HCID 15529569, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl 2-azabicyclo[2.2.1]heptane-3-carboxylate (664 mg, 3.92 mmol) in chloroform (8 ml) were added triethylamine (0.55 ml, 3.92 mmol) and 4-methoxybenzene sulfonyl chloride (892 mg, 4.32 mmol) while being cooled with ice. After a reaction at room temperature for 4 hours, 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 recrystallized (hexane/ethyl acetate), to give ethyl 2-[(4-methoxyphenyl)sulfonyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate (927 mg, 70%).

Workup

  1. temperaturewhile being cooled with ice
  2. customAfter a reaction at room temperature for 4 hours
  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 recrystallized (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-72a673370c5e4f9fa59fd1cd82705b72
Source dataset
uspto-grants-2007_02
Patent number
US07176217B2

Reaction notes

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