1,3-Difluoroacetone → (R)-1-(1,3-difluoropropan-2-yl)pyrrolidin-3-amine

To a solution of (R)-tert-butyl pyrrolidin-3-ylcarbamate (0.500 g) and 1,3-difluoropropan-2-one (0.278 g) in dichloromethane (5 mL) was added sodium triacetoxyborohydride (0.853 g). After stirring for one hour, the reaction was quenched with saturated aqueous NaHCO3 solution (5 mL). The mixture was extracted with dichloromethane (25 mL), and the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting residue was treated with HCl (4.0M in 1,4-dioxane, 4 mL) and methanol (1 mL) and stirred for one hour. The mixture was concentrated to give the title compound.

1. customthe reaction was quenched with saturated aqueous NaHCO3 solution (5 mL)
2. extractionThe mixture was extracted with dichloromethane (25 mL)
3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. additionThe resulting residue was treated with HCl (4.0M in 1,4-dioxane, 4 mL) and methanol (1 mL)
7. stirringstirred for one hour
8. concentrationThe mixture was concentrated

ORD record

ord-0e21f09aec494929b7fcfa7f21033b19

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563735B2