Diethyl Carbonate → (4R)-4-phenyl-1,3-oxazolidin-2-one

HRID 1033131Notes

Reaction equation

HRID 1033131 reaction equation
[NH2:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[C:11](=O)(OCC)[O:12]CC.C([O-])([O-])=O.[K+].[K+]>>[C:5]1([C@@H:2]2[CH2:3][O:4][C:11](=[O:12])[NH:1]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 7766Diethyl CarbonateHCID 11430Potassium CarbonateHCID 2724025(R)-beta-aminophenethyl alcohol

Product 1

HCID 730425(4R)-4-phenyl-1,3-oxazolidin-2-one

Procedure

7.54 g (55 mmol) of (2R)-(-)-2-amino-2-phenylethanol are dissolved in 8 ml (61 mmol) of diethyl carbonate, 770 mg (5.5 mmol) of K2CO3 are added, and ethanol is removed by distillation via a column. The crude product is recrystallized from ether/petroleum ether.

Workup

  1. customethanol is removed by distillation via a column
  2. customThe crude product is recrystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-00e65762665e4fb6b800b9a35748a245
Source dataset
uspto-grants-1994_05
Patent number
US05310499

Reaction notes

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