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-8dde0fd3b5e54743a5023d9d24b5a41c

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045420B2