Sodium Acetate → (2R,3S)-tert-butyl 2-ethyl-3-formylaziridine-1-carboxylate

Participants

Reaction Steps

To a 500 mL round-bottom flask equipped with a stir bar was added (S)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine (2.60 g, 8.00 mmol) and CHCl3 (200 mL). To the solution was added tert-butyl tosylcarbamate (10.9 g, 40.0 mmol). The flask was placed in a room temperature-water bath. To the stirred solution was added sodium acetate (9.84 g, 120 mmol), then (E)-pent-2-enal (4.04 g, 48.0 mmol). The mixture was stirred at room temperature for 40 minutes. The mixture was filtered, washing the filter cake with a small amount of CHCl3. The filtrate was concentrated in vacuo at 30° C. The resulting orange liquid was dissolved in Et2O (400 mL) and transfered to a 1 L separatory funnel. The solution was washed with water:aq. sat. NaHCO3 (200 mL:200 mL). The aqueous phase was extracted with Et2O (100 mL). The combined organics were washed with brine (200 mL); dried over MgSO4; filtered; then concentrated in vacuo to afford (2R,3S)-tert-butyl 2-ethyl-3-formylaziridine-1-carboxylate as a pale orange liquid.

Provenance & Evidence