反应详情

To a mixture of (S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.0 g, 4.36 mmol), (trifluoromethyl)trimethylsilane (2.0 M solution in THF, 2.6 mL, 5.20 mmol) in THF (10 mL) was added tetrabutylammonium fluoride (1.0 M solution in THF, 0.1 mL, 0.10 mmol) at 0° C. After addition, the mixture was stirred at room temperature for 60 h. Then, tetrabutylammonium fluoride (1.0 M solution in THF, 9 mL, 9.0 mmol) was added and the mixture stirred for another 6 h and subsequently quenched by adding saturated aq. NaHCO3 solution, extracted with EtOAc. The extracts were washed with saturated aq. NaHCO3 solution, water, brine and dried over Na2SO4. Concentration and purification gave (S)-tert-butyl 2,2-dimethyl-4-(2,2,2-trifluoro-1-hydroxyethyl)oxazolidine-3-carboxylate (1.21 g, 92%), which showed a complicated NMR spectrum because of the different comformers.

1. additionAfter addition
2. stirringthe mixture stirred for another 6 h
3. customsubsequently quenched
4. additionby adding saturated aq. NaHCO3 solution
5. extractionextracted with EtOAc
6. washThe extracts were washed with saturated aq. NaHCO3 solution, water, brine
7. dry with materialdried over Na2SO4
8. concentrationConcentration and purification