Triethylamine → 1-(Diphenylmethyl)azetidin-3-one

Temperature

10 °C

1-(Diphenylmethyl)azetidin-3-ol (2.0 g) was dissolved in N,N-dimethyl sulfoxide (60 mL), and triethylamine (11.7 mL) was added. The reaction solution was cooled to 10° C., a solution of pyridine sulfur trioxide complex (10.6 g) in N,N-dimethyl sulfoxide (20 mL) was added, and the mixture was stirred for 1 hr. The mixture was warmed to room temperature and further stirred for 3 hr. The reaction solution was poured into cold water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (30% to 50% ethyl acetate/hexane) to give the object product as a white solid (1.83 g, 92.4%).

1. temperatureThe mixture was warmed to room temperature
2. stirringfurther stirred for 3 hr
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over sodium sulfate
6. filtrationThe desiccant was filtered off
7. concentrationthe filtrate was concentrated
8. customThe residue was purified by silica gel column chromatography (30% to 50% ethyl acetate/hexane)

ORD record

ord-ddb2641b19544f92aec134c050ae174a

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575167B2