Sodium Sulfite → 1-Ethyl-4,4-dimethyl-5-oxoproline
Reaction equation
[CH2:1]([N:3]1[CH:7]([CH2:8][OH:9])[CH2:6][C:5]([CH3:11])([CH3:10])[C:4]1=[O:12])[CH3:2].Cl([O-])=[O:14].[Na+].OP([O-])(O)=O.[Na+].CC1(C)N([O])C(C)(C)CCC1.Cl[O-].[Na+].ClCl.S([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[CH2:1]([N:3]1[C:4](=[O:12])[C:5]([CH3:11])([CH3:10])[CH2:6][C@H:7]1[C:8]([OH:14])=[O:9])[CH3:2]Participants
Reactant 7
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
1-Ethyl-5-(hydroxymethyl)-3,3-dimethyl-2-pyrrolidinone (0.366 g, 2.1 mmol), sodium chlorite (0.387 g, 4.3 mmol), and a 1M aqueous sodium phosphate monobasic buffer solution (2.46 ml, 2.46 mmol) were combined in acetonitrile (3 ml) and heated to 40° C. A few crystals of TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy free radical) and approximately 1 drop of bleach (sodium hypochlorite solution, available chlorine >12%) were then added to the mixture and stirring continued at 40° C. for 4 hrs. The mixture was then poured onto ice containing 1% w/w sodium sulphite and the resulting mixture was extracted with ethyl acetate (×3). The combined organic extracts were washed with saturated aqueous sodium chloride and then dried over magnesium sulphate and concentrated to give 1-ethyl-4,4-dimethyl-5-oxoproline (0.392 g) as a white solid which was used without additional purification.
Workup
- extractionthe resulting mixture was extracted with ethyl acetate (×3)
- washThe combined organic extracts were washed with saturated aqueous sodium chloride
- dry with materialdried over magnesium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-13dee41e78884e74b5931a59555677d6
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08048907B2
Reaction notes
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