Sulfoxonium, trimethyl-, iodide (1:1) → Benzyl 8-azaspiro[bicyclo[3.2.1]octane-3,2'-oxirane]-8-carboxylate

To a 500-mL, three-necked, round-bottomed flask equipped with a magnetic stirring bar, a thermometer, and a condenser was charged tetrahydrofuran (163 mL), potassium tert-butoxide (6.6 g, 95% pure) and trimethylsulfoxonium iodide (13.0 g). The mixture was heated to reflux and stirred for 3 hours. A solution of benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (10.0 g) in tetrahydrofuran (37 mL) was added in one portion. The reaction mixture was refluxed for another 2 hours. The mixture was cooled to room temperature and diluted with toluene (100 mL) and water. The water layer was separated and extracted with toluene (2×50 mL). The combined organic layers were washed with water (3×40 mL) and concentrated under vacuum to provide the title compound.

1. customTo a 500-mL, three-necked, round-bottomed flask equipped with a magnetic stirring bar
2. temperatureThe mixture was heated
3. temperatureto reflux
4. temperatureThe reaction mixture was refluxed for another 2 hours
5. customThe water layer was separated
6. extractionextracted with toluene (2×50 mL)
7. washThe combined organic layers were washed with water (3×40 mL)
8. concentrationconcentrated under vacuum

ORDレコード

ord-c157054e46074500a0f7243282a06da7

出典データセット

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09227963B2