Ethyl N-phenylcarbamate → 3-Phenyl-5-methoxymethyloxazolidin-2-one

HRID 650259Notes

Reaction equation

HRID 650259 reaction equation
[C:1]1([NH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[Cs+].[CH3:15][O:16][CH2:17]C1COC(=O)O1>CN(C)C=O>[C:1]1([N:7]2[CH2:12][CH:11]([CH2:15][O:16][CH3:17])[O:10][C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7591Ethyl N-phenylcarbamateHCID 25953Cesium fluorideHCID 43844854-(Methoxymethyl)-1,3-dioxolan-2-one

Product 1

HCID 98371663-Phenyl-5-methoxymethyloxazolidin-2-oneYield 81.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Phenylurethane (15.0 g, 90.9 mmol) was dissolved in N,N-dimethylformamide (40 mL), and thereto were added cesium fluoride (1.15 g, 7.57 mmol) and 4-methoxymethyl-1,3-dioxolan-2-one (10.0 g, 75.7 mol), in order. The mixture was stirred for 50 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 silica gel chromatography to give the subject 3-phenyl-5-methoxymethyloxazolidin-2-one (12.8 g, yield 81.6%).

Workup

  1. filtrationAfter filtering off the insoluble materials
  2. customcondensed in vacuo
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0b0472f1b14547888e3f8cb4b9150cd9
Source dataset
uspto-grants-2001_08
Patent number
US06271388B1

Reaction notes

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