(3S)-3-methyloxolane-2,5-dione

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 600 mg (5.26 mmol) of (3S)-3-methyldihydro-2,5-furandione (preparation: S. G. Davies, D. J. Dixon, J. Chem. Soc., Perkin Trans. 1, 1998, 17, 2635-2643) are introduced to a vessel together with 559 mg (0.77 ml, 5.52 mmol) of triethylamine in 5 ml of dichloromethane at 0° C. and 373 mg (5.52 mmol) of methylamine hydrochloride are added. The reaction mixture is stirred at room temperature overnight and then 938 mg (5.78 mmol) of N,N-carbonyldiimidazole are added in portions. The mixture is stirred at room temperature for 1.5 h and at reflux temperature for 30 minutes. After it has cooled to room temperature the reaction mixture is washed with 5% strength hydrochloric acid and water, the organic phase is dried over magnesium sulfate, filtered and concentrated and the product is dried under a high vacuum. This gives 605 mg of the product (88% of theory). The mixture is stirred at room temperature for 1.5 h at reflux temperature for 30 minutes After it has cooled to room temperature the reaction mixture is washed with 5% strength hydrochloric acid and water the organic phase is dried over magnesium sulfate filtered concentrated the product is dried under a high vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 600 mg (5.26 mmol) of (3S)-3-methyldihydro-2,5-furandione (preparation: S. G. Davies, D. J. Dixon, J. Chem. Soc., Perkin Trans. 1, 1998, 17, 2635-2643) are introduced to a vessel together with 559 mg (0.77 ml, 5.52 mmol) of triethylamine in 5 ml of dichloromethane at 0° C. and 373 mg (5.52 mmol) of methylamine hydrochloride are added. The reaction mixture is stirred at room temperature overnight and then 938 mg (5.78 mmol) of N,N-carbonyldiimidazole are added in portions. The mixture is stirred at room temperature for 1.5 h and at reflux temperature for 30 minutes. After it has cooled to room temperature the reaction mixture is washed with 5% strength hydrochloric acid and water, the organic phase is dried over magnesium sulfate, filtered and concentrated and the product is dried under a high vacuum. This gives 605 mg of the product (88% of theory). The mixture is stirred at room temperature for 1.5 h at reflux temperature for 30 minutes After it has cooled to room temperature the reaction mixture is washed with 5% strength hydrochloric acid and water the organic phase is dried over magnesium sulfate filtered concentrated the product is dried under a high vacuum

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 400 mg (1.46 mmol) 6-bromo-2-phenyl-benzoxazole are dissolved in 15 ml THF and cooled to −70° C., and 1.22 ml (1.92 mmol) n-butyl lithium 1.6M in hexane are added dropwise. This solution chilled to −70° C. is added dropwise to an equally cold −70° C. solution of 220 mg (1.93 mmol) (S)-3-methyl-dihydro-furan-2,5-dione and 15 ml THF. After 15 min stirring the mixture is poured onto semisaturated, acetic acid-containing saline solution and extracted with EA. The org. phase is concentrated by rotary evaporation i. V. and the residue is separated through silica gel (eluant DCM/EA/glacial acetic acid). This solution chilled to −70° C. is poured extracted with EA phase is concentrated by rotary evaporation i and the residue is separated through silica gel (eluant DCM/EA/glacial acetic acid)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 600 mg (5.26 mmol) of (3S)-3-methyldihydro-2,5-furandione (preparation: S. G. Davies, D. J. Dixon, J. Chem. Soc., Perkin Trans. 1, 1998, 17, 2635-2643) are introduced to a vessel together with 559 mg (0.77 ml, 5.52 mmol) of triethylamine in 5 ml of dichloromethane at 0° C., and 373 mg (5.52 mmol) of methylamine hydrochloride are added. The reaction mixture is stirred at room temperature overnight and then 938 mg (5.78 mmol) of N,N-carbonyldiimidazole are added in portions. The mixture is stirred at room temperature for 1.5 h and at reflux temperature for 30 minutes. After it has cooled to room temperature the reaction mixture is washed with 5% strength hydrochloric acid and water, the organic phase is dried over magnesium sulfate, filtered and concentrated and the product is dried under a high vacuum. This gives 605 mg of the product (88% of theory). The mixture is stirred at room temperature for 1.5 h at reflux temperature for 30 minutes After it has cooled to room temperature the reaction mixture is washed with 5% strength hydrochloric acid and water the organic phase is dried over magnesium sulfate filtered concentrated the product is dried under a high vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 600 mg (5.26 mmol) of (3S)-3-methyldihydro-2,5-furandione (preparation: S. G. Davies, D. J. Dixon, J. Chem. Soc., Perkin Trans. 1, 1998, 17, 2635-2643) are introduced to a vessel together with 559 mg (0.77 ml, 5.52 mmol) of triethylamine in 5 ml of dichloromethane at 0° C. and 373 mg (5.52 mmol) of methylamine hydrochloride are added. The reaction mixture is stirred at room temperature overnight and then 938 mg (5.78 mmol) of N,N-carbonyldiimidazole are added in portions. The mixture is stirred at room temperature for 1.5 h and at reflux temperature for 30 minutes. After it has cooled to room temperature the reaction mixture is washed with 5% strength hydrochloric acid and water, the organic phase is dried over magnesium sulfate, filtered and concentrated and the product is dried under a high vacuum. This gives 605 mg of the product (88% of theory). The mixture is stirred at room temperature for 1.5 h at reflux temperature for 30 minutes After it has cooled to room temperature the reaction mixture is washed with 5% strength hydrochloric acid and water the organic phase is dried over magnesium sulfate filtered concentrated the product is dried under a high vacuum