4-Methoxybenzenesulfonyl chloride → ethyl (1S,3R,4R)-2-[(4-methoxyphenyl)sulfonyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate

HRID 347804Notes

Reaction equation

HRID 347804 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 10535139HCID 10535139, compound

Product 1

HCID 86595840ethyl (1S,3R,4R)-2-[(4-methoxyphenyl)sulfonyl]-2-azabicyclo[2.2.1]heptane-3-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl (1S, 3R, 4R)-2-azabicyclo[2.2.1]heptane-3-carboxylate (807 mg, 4.77 mmol) in chloroform (8 ml) were added triethylamine (0.67 ml, 4.77 mmol) and 4-methoxybenzenesulfonyl chloride (1.08 g, 5.25 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 (1S, 3R, 4R)-2-[(4-methoxyphenyl) sulfonyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate (0.965 g, 60%).

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-ceac40d02d9f4fe791f42e8b8f5878b1
Source dataset
uspto-grants-2007_02
Patent number
US07176217B2

Reaction notes

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