Propane sultone → HCID 11425797, compound

The 2-aminoadamantane hydrochloride (2×5 g) was treated with NaOH in water. The aqueous mixture was extracted with dichloromethane. The organic layer was dried over magnesium sulfate. The solvent was removed under reduced pressure. The resulting white solid was dried 30 minutes at room temperature under vacuum. A solution of 1,3-propane sultone (7.4 g, 60 mmol) in THF was added to a solution of the free amine (7.98 g, 52 mmol) in THF (70 mL, total). The mixture was heated under reflux for 4 h, cooled into an ice bath. The solid was collected by filtration, air-dried for 15 min, and further dried in vacuo (11.2 g). Recrystallization was done with methanol/water (60 mL/35 mL). After cooled in a fridge, the solid was collected by filtration, rinsed with methanol, dried in the vacuum oven at 60° C. overnight. A white crystalline sandy solid (small plates, 10.45 g, 74% yield) was obtained. The 1H and 13C NMR were consistent with the structure of Compound BZ.

1. extractionThe aqueous mixture was extracted with dichloromethane
2. dry with materialThe organic layer was dried over magnesium sulfate
3. customThe solvent was removed under reduced pressure
4. customThe resulting white solid was dried 30 minutes at room temperature under vacuum
5. temperatureThe mixture was heated
6. temperatureunder reflux for 4 h
7. temperaturecooled into an ice bath
8. filtrationThe solid was collected by filtration
9. customair-dried for 15 min
10. customfurther dried in vacuo (11.2 g)
11. customRecrystallization
12. temperatureAfter cooled in a fridge
13. filtrationthe solid was collected by filtration
14. washrinsed with methanol
15. customdried in the vacuum oven at 60° C. overnight
16. customA white crystalline sandy solid (small plates, 10.45 g, 74% yield) was obtained

ORD record

ord-182591f2bca14b26ad173cc1daba958e

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642801B2