Cyclopropylamine → (3S,4S)-1-benzyloxycarbonyl-3-cyclopropylaminomethyl-4-fluoropyrrolidine

Temperature

80 °C

(3S,4S)-1-Benzyloxycarbonyl-3-bromomethyl-4-fluoropyrrolidine (415 mg), cyclopropylamine (0.91 mL) and acetonitrile (3 mL) were mixed together. The mixture was stirred at 80° C. for 6 hours and was subsequently concentrated under reduced pressure. To the resulting residue, cyclopropylamine (4.55 mL) was added and the mixture was again stirred at 80° C. for 6 hours and was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (15 mL), washed with saturated brine (2×5 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant: hexane: ethyl acetate=2:1) to give (3S,4S)-1-benzyloxycarbonyl-3-cyclopropylaminomethyl-4-fluoropyrrolidine as a pale brown oil (239 mg).

1. concentrationwas subsequently concentrated under reduced pressure
2. additionTo the resulting residue, cyclopropylamine (4.55 mL) was added
3. stirringthe mixture was again stirred at 80° C. for 6 hours
4. concentrationwas concentrated under reduced pressure
5. dissolutionThe residue was dissolved in ethyl acetate (15 mL)
6. washwashed with saturated brine (2×5 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe resulting residue was purified by silica gel column chromatography (eluant: hexane: ethyl acetate=2:1)

ORD record

ord-8258e299838041548cd04fb568cb2b49

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514451B2