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 1 hour, the reaction was quenched with saturated NaHCO3 solution (5 mL). The product was extracted into dichloromethane (25 mL), dried over magnesium sulfate, filtered, and concentrated. The resulting crude material was treated with HCl (4.0M in dioxane, 4 mL) and methanol (1 mL) and stirred for 1 hour. The mixture was concentrated to provide the title compound.

1. customthe reaction was quenched with saturated NaHCO3 solution (5 mL)
2. extractionThe product was extracted into dichloromethane (25 mL)
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. additionThe resulting crude material was treated with HCl (4.0M in dioxane, 4 mL) and methanol (1 mL)
7. stirringstirred for 1 hour
8. concentrationThe mixture was concentrated

ORD record

ord-d85faf9f686d40bb84065895021148a6

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952157B2