Reaction Steps
To a mixture of N1,N1-dimethylethane-1,2-diamine (74.5 mg, 0.845 mmol), Hunig'sBase (0.369 mL, 2.114 mmol) and DMAP (5.16 mg, 0.042 mmol) in dichloromethane (2 mL) was added (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carbonyl chloride (200 mg, 0.423 mmol). The reaction mixture was stirred for 16 h. LCMS indicated the formation of desired product. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in methanol and the clear solution was purified by prep HPLC to provide the title compound as a colorless oil (150 mg, 68%). LCMS: m/e 525.56 (M+H)+, 2.27 min (method 1). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 6.89 (t, J=5.04 Hz, 1H), 4.72 (d, J=2.14 Hz, 1H), 4.58 (s, 1H), 3.59-3.34 (m, 2H), 3.12 (td, J=11.06, 4.12 Hz, 1H), 2.67 (t, J=5.80 Hz, 2H), 2.53-2.43 (m, 2H), 2.41 (s, 6H), 2.40-2.32 (m, 1H), 2.07-2.03 (m, 1H), 1.97-1.84 (m, 2H), 1.78 (dd, J=11.60, 7.93 Hz, 1H), 1.71 (dd, J=13.12, 2.44 Hz, 1H), 1.67 (s, 3H), 1.62-1.22 (m, 14H), 1.21-1.11 (m, 1H), 1.06 (s, 3H), 1.01 (s, 3H), 1.04-0.97 (m, 1H), 0.97 (s, 6H), 0.91 (s, 3H).
