Pyridine → HCID 57272998, compound

(R)-2-Pyrrolidinemethanol (1.00 g; 9.88 mmol), prepared according to Example 1, and 6 mL methylene chloride were added to a 50 mL, 3-neck round-bottom flask equipped with a reflux condenser topped with a CaCl2 drying tube, an addition funnel and a magnetic stirrer. Pyridine (1.63 mL; 20.16 mmol) was added, and the solution stirred in a room temperature water bath. Thionyl chloride (1.20 g; 10.08 mmol) in 4 mL methylene chloride was added over 15 minutes and washed in with 1 mL methylene chloride. After stirring for 45 minutes at ambient temperature, the reaction mixture was refluxed for 1 hour and then allowed to cool to room temperature and stirred for an additional 2 hours. Hexanes (11 mL) was added and the mixture was stirred in a 0°-5° C. ice bath for 1 hour. After filtration to remove precipitated pyridine hydrochloride, the solvent was removed on a rotary evaporator with a 40° C. water bath to yield 1.47 g (9.88 mmol) of (R)-1-oxo-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,2,3]oxathiazolidine as a brown oil.

1. additionwere added to a 50 mL, 3-neck round-bottom flask
2. customequipped with a reflux condenser
3. customtopped with a CaCl2 drying tube, an addition funnel and a magnetic stirrer
4. washwashed in with 1 mL methylene chloride
5. stirringAfter stirring for 45 minutes at ambient temperature
6. temperaturethe reaction mixture was refluxed for 1 hour
7. temperatureto cool to room temperature
8. stirringstirred for an additional 2 hours
9. additionHexanes (11 mL) was added
10. stirringthe mixture was stirred in a 0°-5° C. ice bath for 1 hour
11. filtrationAfter filtration
12. customto remove
13. customprecipitated pyridine hydrochloride
14. customthe solvent was removed on a rotary evaporator with a 40° C. water bath

ORD record

ord-2a0c937f963148d293f6675f54360134

Source dataset

uspto-grants-1992_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05130432