4-Methoxybenzenesulfonyl chloride → HCID 86595842, compound

HRID 347816Notes

Reaction equation

HRID 347816 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:2]2.C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>C(Cl)(Cl)Cl>[CH3:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([N:2]2[C@@H:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]3[CH2:5][CH2:6][CH:1]2[CH2:8][CH2:7]3)(=[O:31])=[O:30])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 15811783Ethyl (3R)-2-azabicyclo[2.2.2]octane-3-carboxylate

Product 1

HCID 86595842HCID 86595842, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl (3R)-2-azabicyclo[2.2.2]octane-3-carboxylate (362 mg, 1.97 mmol) in chloroform (4.0 ml) were added triethylamine (0.30 ml, 2.17 mmol) and 4-methoxybenzenesulfonyl chloride(448 mg, 2.17 mmol) while being cooled with ice. After a reaction at room temperature for 2 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 (3R)-2-[(4-methoxyphenyl)sulfonyl]-2-azabicyclo[2.2.2]octane-3-carboxylate (261 mg). Further, mother liquid was concentrated, and the resulting residue was purified by silica gel column chromatography (1%–5% methanol/chloroform), to give the same compound (137 mg, total 399 mg, 57%).

Workup

  1. temperaturewhile being cooled with ice
  2. customAfter a reaction at room temperature for 2 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-acf6b01e6513406cb557db98df890c30
Source dataset
uspto-grants-2007_02
Patent number
US07176217B2

Reaction notes

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