Cyclopropylamine → HCID 66705180, compound

Participants

Reaction Conditions

Reaction Steps

(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 subsequently concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (300 mL) and the solution was washed with water (2×50 mL), followed by drying over anhydrous sodium sulfate and concentration under reduced pressure. To the resulting residue, diisopropyl ether (300 mL) was added and the mixture was heated to form crystal and was then concentrated to approximately ½. The formed crystal was collected by filtration and the collected crystal was washed with diisopropyl ether and was dried under reduced pressure to give 4.41 g of (3R,4S)-N-cyclopropyl-4-hydroxymethyl-1-[(1S)-1-phenylethyl]pyrrolidine-3-carboxamide as a white crystal. The filtrate and the washing solution were combined and the combined solvent was concentrated under reduced pressure. The resulting residue was purified on a silica gel column (eluant=hexane:ethyl acetate=1:1, shifted to ethyl acetate) to obtain additional 1.50 g of (3R,4S)-N-cyclopropyl-4-hydroxymethyl-1-[(1S)-1-phenylethyl]pyrrolidine-3-carboxamide. The total amount of the compound was 5.91 g.

Provenance & Evidence