反应详情

温度

-78 °C

To a 1M THF solution of Sodium hexamethyldisylamide (16.2 g, 88.3 mmol) at −78° C. was added via canular a 0° C. solution of (R)-3-((R)-3-methyl-hexanoyl)-4-phenyl-oxazolidin-2-one (18.7 g, 67.9 mmol) in 70 mL dry THF. The resulting solution was stirred at −78° C. for 30 minutes. Methyl Iodide (48.2 g, 339.5 mmol) was added and stirring at −78° C. was continued for 4 hours. The reaction was quenched with saturated ammonium chloride solution, extracted into CH2Cl2 and washed with 1M sodium Bisulfite. The solution was dried over MgSO4, concentrated and chromatographed in 10% ethylacetate in hexane to give the titled compound (11.1 g, 56.5% yield) as an oil. MS, m/z (relative intensity): 1H NMR (400 MHz, CDCl3) δ ppm 0.8 (t, J=7.0 Hz, 3H) 0.9 (d, J=6.6 Hz, 3H) 1.0 (d, J=6.8 Hz, 3H) 1.0 (d, J=8.5 Hz, 1H) 1.1 (m, 1H) 1.4 (m, 1H) 1.7 (m, 1H) 3.7 (m, 1H) 4.2 (dd, J=8.8, 3.4 Hz, 1H) 4.6 (t, J=8.7 Hz, 1H) 5.4 (dd, J=8.7, 3.3 Hz, 1H) 7.2 (m, 2H) 7.3 (m, 3H). MS, m/z (relative intensity):290 [M+1H, 100%].

1. stirringstirring at −78° C.
2. waitwas continued for 4 hours
3. customThe reaction was quenched with saturated ammonium chloride solution
4. extractionextracted into CH2Cl2
5. washwashed with 1M sodium Bisulfite
6. dry with materialThe solution was dried over MgSO4
7. concentrationconcentrated
8. customchromatographed in 10% ethylacetate in hexane