Triethylamine → HCID 68430090, compound

HRID 1931296Notes

Reaction equation

HRID 1931296 reaction equation
C(N(CC)CC)C.[CH2:8]([S:12](Cl)(=[O:14])=[O:13])[CH2:9][CH2:10][CH3:11].I.[CH:17]12[CH2:28][CH2:27][CH:20]([CH2:21][CH:22]1[C:23]([O:25][CH3:26])=[O:24])[CH2:19][NH:18]2>C(Cl)(Cl)Cl>[CH2:8]([S:12]([N:18]1[CH2:19][C@H:20]2[CH2:27][CH2:28][C@@H:17]1[C@H:22]([C:23]([O:25][CH3:26])=[O:24])[CH2:21]2)(=[O:14])=[O:13])[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 754301-Butanesulfonyl chlorideHCID 68430326HCID 68430326, compound

Product 1

HCID 68430090HCID 68430090, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (0.51 mL, 3.7 mmol) and 1-butanesulfonyl chloride (0.233 mL, 1.84 mmol) were added to a chloroform (5 mL) solution of methyl 2-azabicyclo[2.2.2]octane-6-carboxylate hydroiodide (298 mg, 0.989 mmol) synthesized according to the method described in literature (Chem. Pharm. Bull. 53(1) 81-85 (2005)), and the mixture was stirred at room temperature for 13 hours. The reaction mixture was washed once with distilled water, and once with a saturated sodium hydrogen carbonate aqueous solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was then purified using silica gel column chromatography to obtain the target (157 mg, 55%).

Workup

  1. customsynthesized
  2. washThe reaction mixture was washed once with distilled water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was then purified
  6. customto obtain the target (157 mg, 55%)

Sources & evidence

ORD record
ord-87ced0115f994936b06e2dffb7e26c0f
Source dataset
uspto-grants-2012_05
Patent number
US08188280B2

Reaction notes

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