Sodium Bicarbonate → HCID 16098104, compound

Participants

Reaction Steps

The title compound was prepared using commercially available ethyl chloro oximidoacetate (5). N-Boc-pyrroline (1.0 g; 5.91 mmol), ethyl chloro oximidoacetate (2.55 g; 16.8 mmol) and sodium bicarbonate (1.77 g; 21.06 mmol) in ethyl acetate (15 mL) were stirred for 54 hours. An additional amount of chloro oxime (2.6 g; 17.28 mmol) and sodium bicarbonate (2.1 g; 25.00 mmol) was added and the reaction mixture stirred overnight. The addition of reagents was repeated again and the reaction mixture stirred for 36 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was washed with water, brine, dried (MgSO4), filtered and evaporated. Cycloadduct 6 was isolated as a clear oil after chromatography with 20% ethyl acetate/hexanes.

Provenance & Evidence