1,1-Dichloroethane → HCID 86755480, compound

Participants

Reaction Steps

A mixture of cis-2,3,3a,4,9,9a-hexahydro-5-methoxy-1H-benz[f]indole (D17, 0.08 g, 0.39 mmol), 4-(4-phenylbenzoylamino)butyraldehyde (0.11 g, 0.40 mmol), and sodium triacetoxyborohydride (0.13 g, 0.61 mmol) in dichioroethane (20 ml), was stirred at room temperature for 18 h. Resulting mixture was partitioned between saturated aqueous NaHCO3 (20 ml) and dichloromethane (3×10 ml). The combined extracts were dried (Na2SO4) and evaporated in vacuo to give an oil. Chromatography on silica using 0-4% methanol-dichloromethane gradient elution gave the free base of the title compound as a colourless solid (0.07 g, 38%). The free base was treated with 1M ethereal HCl (0.31 ml, 0.3 mmol) in dry dichloromethane to afford after evaporation the title compound.

Provenance & Evidence