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

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.

1. customTo a 500 mL round-bottom flask equipped with a stir bar
2. customwas placed in a room temperature
3. filtrationThe mixture was filtered
4. washwashing the filter cake with a small amount of CHCl3
5. concentrationThe filtrate was concentrated in vacuo at 30° C
6. dissolutionThe resulting orange liquid was dissolved in Et2O (400 mL)
7. customtransfered to a 1 L separatory funnel
8. washThe solution was washed with water
9. extractionThe aqueous phase was extracted with Et2O (100 mL)
10. washThe combined organics were washed with brine (200 mL)
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationthen concentrated in vacuo

ORD-Eintrag

ord-74e9e9d7f9554b9fa6d24097e1c753d9

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09334279B2