Potassium Carbonate → (4S)-4-Benzyl-5,5-dimethyl-1,3-oxazolidin-2-one

HRID 2392828Notes

Reaction equation

HRID 2392828 reaction equation
[CH2:1]([C@H:8]([NH:13][C:14](=[O:19])C(Cl)(Cl)Cl)[C:9]([OH:12])([CH3:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:1]([C@H:8]1[C:9]([CH3:11])([CH3:10])[O:12][C:14](=[O:19])[NH:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67617846HCID 67617846, compound

Product 1

HCID 10921652(4S)-4-Benzyl-5,5-dimethyl-1,3-oxazolidin-2-oneYield 77.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (9) (4.093 g, 12.63 mmol) in ethanol (280 ml) was added potassium carbonate (0.872 g, 6.32 mmol) and the solution was refluxed for 30 minutes. After concentration in vacuo, dichloromethane was added and the mixture was washed with saturated aqueous sodium chloride solution. Concentration in vacuo gave crude crystalline solid which was purified by recrystallisation in diethyl ether/40-60 petroleum ether to give the title compound (10) (2.003 g, 77%); mp 59° C.; νmax (CHCl3) 1753 cm-1 ; [α]D25 (c 0.6 in CHCl3)=-103.5; (Found: C, 70.52; H. 7.09; N, 6.52. C12H15NO2 requires C, 70.22; H, 7.37; N, 6.82%); δH (200 MHz; CDCl3) 1.45 (6H, s, C(CH3)2), 2.64-2.88 (2H, m, CH2Ph), 3.72 (1H, dd, J=4.5 and 10.9, CHCH2), 5.45 (1H, s, NH), 7.18-7.38 (5H1 m, ArCH); δC (125 MHz; CDCl3) 21.82 (CH3), 27.42 (CH3), 36.99 (CH2), 63.08 (CH), 83.28 (C), 127.32 (CH), 129.08 (CH), 129.22 (CH), 137.19 (C), 158.47 (CO); m/z (CI+, NH3) 206 (M+ +1).

Workup

  1. temperaturethe solution was refluxed for 30 minutes
  2. concentrationAfter concentration in vacuo, dichloromethane
  3. additionwas added
  4. washthe mixture was washed with saturated aqueous sodium chloride solution
  5. concentrationConcentration in vacuo
  6. customgave crude crystalline solid which
  7. customwas purified by recrystallisation in diethyl ether/40-60 petroleum ether

Sources & evidence

ORD record
ord-b17c790a8a0a4d97b077d7baf038c017
Source dataset
uspto-grants-1998_09
Patent number
US05801249

Reaction notes

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