Hydrochloric Acid → (3S)-3-hydrazino-1-methylpyrrolidine dihydrochloride

To a mixture of (3R)-1-methylpyrrolidin-3-ol and 35 mL of tetrahydrofuran was added 18.2 g of triphenylphosphine, and a solution of 13.2 g of di-tert-butyl azodicarboxylate in 10 mL of a tetrahydrofuran was added dropwise thereto under ice-cooling, followed by stirring for 1 hour, and further stirring at room temperature for 1 hour. To the reaction mixture was added 40 mL of a 6 M hydrochloric acid, followed by stirring at room temperature overnight. To the reaction mixture was added 40 mL of water, tetrahydrofuran was evaporated under reduced pressure, and then 20 mL of dichloromethane was added thereto and the organic layer was separated. The obtained aqueous layer was washed with 20 mL of dichloromethane twice, and the aqueous layer was evaporated under reduced pressure, and then coevaporated with isopropanol. After forming a precipitate, the obtained solid was collected by filtration and dried under reduced pressure to obtain 7.92 g of (3S)-3-hydrazino-1-methylpyrrolidine dihydrochloride.

1. temperatureunder ice-cooling
2. stirringfurther stirring at room temperature for 1 hour
3. stirringby stirring at room temperature overnight
4. customwas evaporated under reduced pressure
5. addition20 mL of dichloromethane was added
6. customthe organic layer was separated
7. washThe obtained aqueous layer was washed with 20 mL of dichloromethane twice
8. customthe aqueous layer was evaporated under reduced pressure
9. customAfter forming a precipitate
10. filtrationthe obtained solid was collected by filtration
11. customdried under reduced pressure

ORD record

ord-3dfa8c3ef98748bc880ae812f7d3764e

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822448B2