Carbon Dioxide → 3-[Cycloprop-2-en-1-oyl]-oxazolidinone

A flame-dried 100 mL round bottomed flask containing 6 (84 mg, 1.0 mmol), 20 mL of THF was chilled by a cold bath at −30° C. (dry ice/30% ethanol in ethylene glycol). The mixture was allowed to stir under nitrogen atmosphere. Distilled triethylamine (0.36 g, 0.50 mL, 3.5 mmol), 1-adamantyl chloride (238 mg, 1.2 mmol) were added sequentially, and stirring at −30° C. was continued for one hour. LiCl (0.21 g, 5.0 mmol) was added. After five minutes, oxazolidinone (131 mg, 1.50 mmol), and 4-dimethylamino pyridine (13 mg, 0.10 mmol) were added. The whole reaction mixture was allowed to stir overnight at room temperature. The solvents were removed under reduced pressure, and the residue was partitioned between 20 mL of CH2Cl2 and 20 mL water. The aqueous layer was extracted twice with 20 mL portions of CH2Cl2, and the combined organics were dried (Na2SO4), filtered, and concentrated. The residue was chromatographed on silica gel. The eluent was 1:3:6 CH2Cl2:ethyl acetate:hexane. The yield of 8 was 115 mg (0.752 mmol, 75%). Compound 8 is a semi-solid.

1. stirringstirring at −30° C.
2. waitAfter five minutes
3. customThe whole reaction mixture
4. stirringto stir overnight at room temperature
5. customThe solvents were removed under reduced pressure
6. customthe residue was partitioned between 20 mL of CH2Cl2 and 20 mL water
7. extractionThe aqueous layer was extracted twice with 20 mL portions of CH2Cl2
8. dry with materialthe combined organics were dried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was chromatographed on silica gel

ORDレコード

ord-bc634514459141788df14357678a50cd

出典データセット

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08236949B2