Potassium Carbonate → (4S,5R)-3-(1-oxo-4-methylpentyl)-4-methyl-5-phenyl-2-oxazolidinone

Temperature

0 °C

To a solution of (4S,5R)-4-methyl-5-phenyl-2-oxazolidinone (9.7 g) [prepared according to the procedures in Evans, D. A.; Mathre, D. J.; Scott, W. L. J. Org. Chem. 1985, 50, 1830-1835] in 100 mL of THF cooled to -78° C. with stirring, was added 35.6 mL of n-butyllithium (1.6M in hexane) until the orange-red color of the di-anion just persisted. The reaction mixture was then treated with 7.0 mL (7.7 g) of distilled 4-methylpentanoyl chloride, warmed to 0° C. and stirred for 30 min. Then 20 mL of 1M aqueous K2CO3 was added and the resultant two-phase mixture was stirred at 25° C. for 1 h. The organic solvents were evaporated in vacuo and the residue was extracted twice with CH2Cl2. The combined organic extract was washed with water and brine, then was dried over Na2SO4 and evaporated. The residue was subjected to flash chromatography on silica gel (hexane-EtOAc) to give 14.5 g (97% yield) of (4S,5R)-3-(1-oxo-4-methylpentyl)-4-methyl-5-phenyl-2-oxazolidinone as a solid. Characteristic analytical data are as follows: mp 76°-77° C. (hexane/EtOAc); 1H NMR (300 MHz, CDCl3) δ7.30-7.46 (m, 5H), 5.67 (d, J=8 Hz, 1H), 4.77 (p, J=7 Hz, 1H), 2.88-3.05 (m, 2H), 1.53-1.69 (m, 3H), 0.94 (d, J=7 Hz, 6H), 0.90 (d, J=7 Hz, 3H); [α]25D -33° (c=1.07, CH2Cl2).

1. stirringstirred for 30 min
2. customThe organic solvents were evaporated in vacuo
3. extractionthe residue was extracted twice with CH2Cl2
4. extractionThe combined organic extract
5. washwas washed with water and brine
6. dry with materialwas dried over Na2SO4
7. customevaporated

ORD record

ord-fc527275122b408f8bfac14ab19d1dd9

Source dataset

uspto-grants-1995_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05470834