Triethylamine → [(1S,4aS,7R)-1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-1-phenanthrenyl](1-pyrrolidinyl)methanone

Participants

Reaction Steps

A solution of acanthoic acid 1 (30 mg, 0.10 mmol) in CH2Cl2 (3.0 ml) was treated with oxalyl chloride (0.013 ml, 0.15 mmol) in the presence of a catalytic amount of DMF at room temperature. The reaction mixture was stirred for 3 h at room temperature, distilled under reduced pressure, and then 3 ml of CH2Cl2 was added. Triethylamine (0.03 ml, 0.20 mmol) and pyrrolidine (0.02 ml, 0.20 mmol) were added to the reaction mixture. The reaction mixture was stirred for 30 min., quenched with water and extracted with 5 ml of CH2Cl2. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10) to afford 25 mg of the analog 2 (71%).

Provenance & Evidence