Boron trifluoride → (R)-1-(1-Benzylpyrrolidin-3-YL)cyclopropanamine

(3R)-3-Cyano-1-benzylpyrrolidine (1.40 g) was dissolved in tetrahydrofuran (21.0 mL) under an argon atmosphere. Titanium(IV) tetraisopropoxide (2.40 mL) and ethylmagnesium bromide (5.00 mL, 3 mol/L solution in ether) were added to the solution at room temperature. After 0.5 h, trifluoroboron.diethyl ether complex (1.90 mL) was added dropwise to the mixture, and the resultant mixture was stirred at room temperature. After 4 h, 2 mol/L aqueous sodium hydroxide (30 mL) was added to the reaction mixture, followed by stirring for 0.25 hours. The product that precipitated was collected through filtration and then extracted. The formed aqueous layer was again extracted with ethyl acetate, and the organic layers were combined together, washed with saturated brine, and dried over sodium sulfate. The drying agent was removed through filtration, and the filtrate was concentrated under reduced pressure, to thereby the target compound as a crude product (1.65 g).

1. additiondiethyl ether complex (1.90 mL) was added dropwise to the mixture
2. waitAfter 4 h
3. customThe product that precipitated
4. filtrationwas collected through filtration
5. extractionextracted
6. extractionThe formed aqueous layer was again extracted with ethyl acetate
7. washwashed with saturated brine
8. dry with materialdried over sodium sulfate
9. customThe drying agent was removed through filtration
10. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-f9e8bfabf2364e1fa59c4c91e2a8cc6c

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07994344B2