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

HRID 354167Notes

Reaction equation

HRID 354167 reaction equation
CS(O[CH:6]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)(=O)=O.[I-:17].[K+]>CN(C)C=O>[I:17][CH:6]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1

Participants

4

Reactant 2

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

Product 1

HCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of tert-butyl 3-[(methylsulfonyl)oxy]-1-azetidinecarboxylate (prepared as described in Synlett 1998, 379; 5.0 g, 19.9 mmol), and potassium iodide (16.5 g, 99.4 mmol) in N,N-dimethylformamide (25 mL), was heated at 10° C. for 42 h. The cooled mixture was partitioned between water and ethyl acetate, and the layers separated. The organic phase was dried over MgSO4, concentrated under reduced pressure and the residue azeotroped with xylene. The crude product was purified by flash column chromatography (dichloromethane as eluant) to give the title compound, 3.26 g.

Workup

  1. customThe cooled mixture was partitioned between water and ethyl acetate
  2. customthe layers separated
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customthe residue azeotroped with xylene
  6. customThe crude product was purified by flash column chromatography (dichloromethane as eluant)

Sources & evidence

ORD record
ord-bd1f6ae74c884752b6f993b8ef4d21ab
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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