Carbamic acid, ethyl ester → (R)-5-(Methoxymethyl)oxazolidin-2-one
Reaction equation
[NH2:1]C(OCC)=O.[F-].[Cs+].[CH3:9][O:10][CH2:11][C@H:12]1[CH2:16][O:15][C:14](=O)[O:13]1>CN(C)C=O>[CH3:9][O:10][CH2:11][C@@H:12]1[O:13][C:14](=[O:15])[NH:1][CH2:16]1Participants
5
Conditions
- Temperature
- 140 °C
Procedure
Urethane (37.4 g, 0.420 mmol) was dissolved in N,N-dimethylformamide (200 mL), and thereto were added cesium fluoride (5.80 g, 38.2 mmol) and (S)-4-methoxymethyl-1,3-dioxolan-2-one (50 g, 0.382 mol, optical purity 97.7%ee), in order. The mixture was stirred for 72 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 (35.1 g, yield 69.6 %, optical purity 97.3%ee).
Workup
- filtrationAfter filtering off the insoluble materials
- customcondensed in vacuo
- distillationthe residue was purified by distillation
Sources & evidence
- ORD record
- ord-0c9cf11626ce4ed4be3fbc029e2feee6
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06271388B1
Reaction notes
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