Potassium Iodide → Tert-butyl 3-iodoazetidine-1-carboxylate

HRID 1427044Notes

Reaction equation

HRID 1427044 reaction equation
[I-:1].[K+].CS(O[CH:8]1[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]1)(=O)=O>CS(C)=O.C(OCC)C.O>[I:1][CH:8]1[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]1

Participants

6

Reactant 2

HCID 4875Potassium IodideHCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate

Product 1

HCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylateYield 68%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
140 °C

Procedure

Potassium iodide (51.0 g, 307 mind) was added to a solution of tert-butyl 3-((methylsulfonyl)oxy)azetidine-1-carboxylate described in Production Example 26-2 (7.72 g, 30.7 mmol) in dimethylsulfoxide (80 mL) under nitrogen atmosphere at room temperature, and the mixture was stirred at 140° C. for 2 hours. The reaction liquid was diluted with diethyl ether and water. The aqueous layer was extracted with diethyl ether. The combined organic layer was washed serially with an aqueous sodium pyrosulfite solution and a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the resultant was concentrated under vacuum. The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate 9:1-1:1) to obtain the title compound (5.91 g, 68%).

Workup

  1. customThe reaction liquid
  2. extractionThe aqueous layer was extracted with diethyl ether
  3. washThe combined organic layer was washed serially with an aqueous sodium pyrosulfite solution
  4. dry with materiala saturated saline solution and then dried over anhydrous sodium sulfate
  5. customThe drying agent was separated by filtration
  6. concentrationthe resultant was concentrated under vacuum
  7. customThe residue was purified with silica gel column chromatography (n-heptane:ethyl acetate 9:1-1:1)

Sources & evidence

ORD record
ord-7989b09c3c77409a9d0cf5bdefd9dbd9
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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