Urea → (R)-5-(Methoxymethyl)oxazolidin-2-one
Reaction equation
[NH2:1]C(N)=O.[F-].[Ce+3].[F-].[F-].[CH3:9][O:10][CH2:11][C@H:12]1[CH2:16][O:15][C:14](=O)[O:13]1>CS(C)=O>[CH3:9][O:10][CH2:11][C@@H:12]1[O:13][C:14](=[O:15])[NH:1][CH2:16]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
Urea (246 g, 4.09 mmol) was dissolved in dimethyl sulfoxide (2.27 L), and thereto were added cerium fluoride (69.0 g, 0.454 mol) and (S)-4-methoxymethyl-1,3-dioxolan-2-one (600 g, 4.54 mol, optical purity 98.9%ee), in order. The mixture was stirred for 36 hours at 140° C. under an atmosphere of argon. After filtering off the insoluble materials, the filtrate was condensed in vacuo, and the residue was purified by distillation to give the subject (R)-5-methoxymethyloxazolidin-2-one (445 g, yield 74.7%, optical purity 98.6%ee).
Workup
- filtrationAfter filtering off the insoluble materials
- customcondensed in vacuo
- distillationthe residue was purified by distillation
Sources & evidence
- ORD record
- ord-528ea58f7b5348a887c0f6364be9a941
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06271388B1
Reaction notes
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