1-Butanaminium, N,N,N-tributyl-, azide → (S)-3-Azido-4,4-dimethyldihydrofuran-2(3H)-one

HRID 1174395Notes

Reaction equation

HRID 1174395 reaction equation
FC(F)(F)S(O[C@@H:7]1[C:11]([CH3:13])([CH3:12])[CH2:10][O:9][C:8]1=[O:14])(=O)=O.[N-:17]=[N+:18]=[N-:19].C([N+](CCCC)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.CCOCC>[N:17]([C@H:7]1[C:11]([CH3:13])([CH3:12])[CH2:10][O:9][C:8]1=[O:14])=[N+:18]=[N-:19]

Participants

5

Reactant 2

HCID 57432321-Butanaminium, N,N,N-tributyl-, azideHCID 10106752(R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl trifluoromethanesulfonate

Product 1

HCID 10057735(S)-3-Azido-4,4-dimethyldihydrofuran-2(3H)-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution containing the product from Example 174A (4.6 g, 17.56 mmol) in toluene (80.0 mL) was added tetra-n-butylammonium azide (5.0 g, 17.57 mmol) at room temperature, and the mixture was stirred for 5 hours. The reaction was diluted with ether and washed with water, dilute NaHCO3, 10% citric acid and brine. The organic layer was dried over MgSO4, filtered and concentrated to give the crude product, which was used without further purification (2.79 g).

Workup

  1. washwashed with water, dilute NaHCO3, 10% citric acid and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a5df6eee4331436b851fd7a0e0d03686
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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