4-Methylmorpholine → HCID 67092960, compound

Participants

Reaction Steps

A solution of (2R,5S)-2-allyl-5-{[benzyloxycarbonyl-(2-tert-butoxycarbonyl-ethyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (875 mg, 1.74 mmol) in hydrogen chloride solution (4 M in 1,4-dioxane) was stirred for 21/2 h at room temperature, then concentrated in vacuo. The residue was taken up in N,N-dimethylformamide (10 mL), then 4-methylmorpholine (528 mg, 5.23 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (993 mg, 2.61 mmol) were added. The reaction mixture was stirred for 16 h at room temperature, then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) afforded the title compound (479 mg, 84%). Colourless gum, MS: 329.4 (M+H)+.

Provenance & Evidence