(R)-(+)-4-Isopropyl-2-oxazolidinone synthesis
- Product Name:(R)-(+)-4-Isopropyl-2-oxazolidinone
- CAS Number:95530-58-8
- Molecular formula:C6H11NO2
- Molecular Weight:129.16
4276-09-9
124-38-9
95530-58-8
To a dry Schlenk tube containing DMSO-d6 (1 mL) and cesium carbonate (33 mg, 0.1 mmol) was added (S)-1a (0.1114 mL, 1 mmol). The reaction mixture was frozen in a liquid nitrogen bath (-196 °C), followed by evacuation to remove air and replacement with CO2 gas. After thawing to 25 °C, a balloon (1 L) containing CO2 was connected to the reaction tube. The reaction system was stirred at 150°C for 24 hours. Upon completion of the reaction, the crude product was analyzed by 1H NMR and the yield was calculated using the internal standard N,N-dimethylformamide as reference. Subsequently, DMSO-d6 was removed by distillation under reduced pressure conditions (6 mmHg, 50 °C).The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate, 3:1) to afford the target product (S)-4-isopropyloxazolidin-2-one ((S)-2a) as a white solid in 80% isolated yield (103.3 mg, 0.80 mmol).
4276-09-9
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124-38-9
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95530-58-8
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Yield:95530-58-8 70%
Reaction Conditions:
with caesium carbonate in dimethylsulfoxide-d6 at 25 - 150; under 760.051 Torr; for 24 h;Schlenk technique;
Steps:
Typical procedure for oxazolidinone synthesis
To a DMSO-d6 (1 mL) solution of cesium carbonate (33 mg, 0.1 mmol) was added (S)-1a (0.1114 mL, 1 mmol). A dried glass Schlenk tube containing the reaction mixture was frozen with liquid nitrogen (-196 °C) under vacuum for air removal, then purged with CO2 gas and thawed at 25 °C. A balloon (1 L) filled with CO2 was fitted to the glass tube. The glass tube was stirred at 150 °C for 24 h. Upon completion, the reaction mixture was subjected to 1H NMR for crude product yield determination, which calculated based on the ratio between product and internal standard (N,N-dimethylformamide). After that, DMSO-d6 was removed through distillation undervacuum conditions (6 mmHg, 50 °C); the syrupy product was then purified bycolumn chromatography on silica gel (hexane/ethyl acetate 3:1) to give the product (S)-4-isopropyloxazolidin-2-one (S)-2a as white solids with an isolated yield of 80% (103.3 mg, 0.80 mmol).
References:
Foo, Siong Wan;Takada, Yuki;Yamazaki, Yusuke;Saito, Susumu [Tetrahedron Letters,2013,vol. 54,# 35,p. 4717 - 4720] Location in patent:supporting information
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95530-58-8
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95530-58-8
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