Ethylenediamine → HCID 18317241, compound

Participants

Reaction Conditions

Reaction Steps

Under Ar, a solution of 42 (3.35 g, 11.3 mmol) in EtOH (150 mL) was treated with ethylene diamine (0.9 g, 15 mmol) and heated at 50° C. After 3 h, the reaction was concentrated to dryness and the residue was partitioned between H2O and EtOAc (3×). The combined organic extracts were dried, filtered and concentrated to dryness. The residue was dissolved in toluene (230 mL) and reacted with DDQ (4.0 g, 17.6 mmol). After 18 h at room temperature, the reaction was heated at 60° C. for 2 h then treated with additional DDQ (1.0 g) and heated at 80° C. for 5 h. The reaction was then dry packed with silica gel (70 g) and chromatographed on a Still column (80 mm). The product was eluted with 30% EtOAc-hexanes to yield 2.85 g of 43.

Provenance & Evidence