Bis-(1H-imidazol-2-YL)-methanone → (S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone
Reaction equation
[NH2:1][C@@H:2]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([CH3:6])([OH:5])[CH3:4].[C:14](C1NC=CN=1)(C1NC=CN=1)=[O:15]>ClCCl>[CH2:7]([C@H:2]1[C:3]([CH3:4])([CH3:6])[O:5][C:14](=[O:15])[NH:1]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (8) (16.27 g, 90.9 mmol) in dichloromethane (1 1) was added carbonyl diimidazole (17.69 g, 109.1 mmol) and the reaction mixture was refluxed for 2 hours. The reaction was quenched with hydrochloric acid (1M) and the product extracted repeatedly with dichloromethane. The combined organic extracts were dried over magnesium sulphate. After concentration in vacuo the residue was purified by flash column chromatography using 40% ethyl acetate/40-60 petroleum ether as eluant to give the title compound (10) (17.89 g, 96%).