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

HRID 393901Notes

Reaction equation

HRID 393901 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-carboxylateYield 57.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °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 100° C. for 42 h. The cooled to 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, 11.5 mmol).

Workup

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

Sources & evidence

ORD record
ord-9239576e1d9d428baac0e2d43fa92b5f
Source dataset
uspto-grants-2004_10
Patent number
US06809200B2

Reaction notes

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