4-Methoxybenzenesulfonyl chloride → HCID 86595839, compound

HRID 347801Notes

Reaction equation

HRID 347801 reaction equation
[C@H:1]12[CH2:7][C@H:4]([CH2:5][CH2:6]1)[C@@H: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[C@H:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C@@H:4]3[CH2:7][C@H: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 11183347HCID 11183347, compound

Product 1

HCID 86595839HCID 86595839, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl (1R, 3S, 4S)-2-azabicyclo[2.2.1]heptane-3-carboxylate (0.724 g, 4.28 mmol) in chloroform (8 ml) was added triethylamine (0.60 ml, 4.28 mmol) and 4-methoxybenzenesulfonyl chloride (0.973 g, 4.71 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 (1R, 3S, 4S)-2-[(4-methoxyphenyl)sulfonyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate (1.04 g, 71%).

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-64288e9dc381458d8b850ad2c26aa86b
Source dataset
uspto-grants-2007_02
Patent number
US07176217B2

Reaction notes

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