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

HRID 1838943Notes

Reaction equation

HRID 1838943 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
100 °C

Procedure

A mixture of tert-butyl 3-[(methylsulphonyl)oxy]-1-azetidinecarboxylate (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 hours. The cooled mixture was partitioned between water and ethyl acetate, and the layers separated. The organic phase was dried (MgSO4), concentrated under reduced pressure and the residue azeotroped with xylene. The crude product was purified by column chromatography on silica gel using 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 (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customthe residue azeotroped with xylene
  6. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-00dcf89b49ff43f1a8766d74cd14dca4
Source dataset
uspto-grants-2004_01
Patent number
US06677335B1

Reaction notes

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