Chloride → HCID 10241129, compound

Temperature

0 °C

IPA (11 L) was added to pyridine (1850 g; 1890 mL) at 20° C. with stirring for 1 hour. The solution was cooled to between −10° C. and 2° C. and cyclopropane sulfonic chloride (1100 g) was added dropwise followed by stirring at this temperature for 70 hours. NMR analysis showed 85% of sulfonic chloride was consumed in the reaction. The reaction was cooled to 0° C. and NaOH (312 g) in water (600 mL) was added dropwise. The resultant product was concentrated to dryness and 45° C. and diluted with EtOAc (2750 mL), MTBE (1375 mL). The solution was stirred for 10 minutes and filtered. Heptane (1375 mL) was added, filtered and the filtrate was concentrated to dryness giving 1080 g of product as a red liquid (84% yield). 1H NMR (CDCl3, 400 MHz): δ 4.86 (m, 1H), 2.83 (m, 1H), 1.33 (d, 6H), 0.98-1.10 (m, 4H).

1. temperatureThe solution was cooled to between −10° C. and 2° C.
2. stirringby stirring at this temperature for 70 hours
3. customwas consumed in the reaction
4. additionNaOH (312 g) in water (600 mL) was added dropwise
5. concentrationThe resultant product was concentrated to dryness and 45° C.
6. additiondiluted with EtOAc (2750 mL), MTBE (1375 mL)
7. stirringThe solution was stirred for 10 minutes
8. filtrationfiltered
9. additionHeptane (1375 mL) was added
10. filtrationfiltered
11. concentrationthe filtrate was concentrated to dryness

ORD record

ord-79a5af2ec5fe4c8dbbcd41ef840fa4c4

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08470878B2