Potassium Carbonate → (S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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).