Cyclopropylamine → HCID 66705180, compound

Temperature

80 °C

(1S,5R)-7-[(1R)-1-Phenylethyl]-3-oxa-7-azabicyclo[3.3.0]octane-2-one (7.73 g, 33.4 mmol) was dissolved in ethanol (92 mL). To this solution, cyclopropylamine (46.3 ml) was added and the mixture was stirred at 80° C. for 44 hours and was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (300 mL), washed with water (2×50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Diisopropylether (300 mL) was added to the residue and the solution was heated to form crystals. The solution was concentrated to approximately half the original volume and the crystals formed were filtered. The collected crystals were washed with diisopropyl ether and were dried under reduced pressure to give (3R,4S)—N-cyclopropyl-4-hydroxymethyl-1-[(1S)-1-phenylethyl]pyrrolidine-3-carboxamide as white crystals (4.41 g). The filtrate and the washings were then combined and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant: hexane:ethyl acetate=1:1->ethyl acetate) to give additional (3R,4S)—N-cyclopropyl-4-hydroxymethyl-1-[(1S)-1-phenylethyl]pyrrolidine-3-carboxamide (1.50 g).

1. concentrationwas concentrated under reduced pressure
2. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
3. washwashed with water (2×50 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. additionDiisopropylether (300 mL) was added to the residue
7. temperaturethe solution was heated
8. customto form crystals
9. concentrationThe solution was concentrated to approximately half the original volume
10. customthe crystals formed
11. filtrationwere filtered
12. washThe collected crystals were washed with diisopropyl ether
13. customwere dried under reduced pressure

ORD record

ord-7dcd753ad46e402cbe24e6490731902a

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106072B2