Reaction #85636

Reaction equation

Imidazole

(S)-4-(hydroxymethyl)oxazolidin-2-one

tert-butylchlorodiphenylsilane

→

(R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)oxazolidin-2-one

Yield 78.0%

Solvents

DCM

water

Conditions

Workup

1. 1
   OtherA white precipitate formed
2. 2
   OtherThe layers were separated
3. 3
   Extractionthe aqueous layer was extracted with DCM (50 mL)
4. 4
   WashThe combined organic extracts were washed with saturated aqueous sodium chloride (50 mL)
5. 5
   Dryingdried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated

Procedure

Imidazole (1.74 g, 25.6 mmol, 2.0 equiv) was added to a solution of (S)-4-(hydroxymethyl)oxazolidin-2-one (1.5 g, 12.8 mmol) and tert-butylchlorodiphenylsilane (3.95 mL, 15.4 mmol, 1.2 equiv) in DCM (43 mL) at room temperature. A white precipitate formed. The solution was stirred at room temperature for 16 hours and then diluted with water (50 mL). The layers were separated and the aqueous layer was extracted with DCM (50 mL). The combined organic extracts were washed with saturated aqueous sodium chloride (50 mL), dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/Heptane 20 to 65%) provided (R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)oxazolidin-2-one (3.55 g, sticky colorless oil) in 78% yield. 1H NMR (400 MHz, CDCl3) δ 7.64 (m, 4H), 7.50-7.38 (m, 6H), 5.31 (m, 1H), 4.44 (t, J=8.7 Hz, 1H), 4.15 (m, 1H), 4.00 (m, 1H), 3.65 (d, J=5.5 Hz, 2H), 1.07 (s, 9H). MS m/z 356.1 (M+H)+; Rt-1.00 min.

Source