Ethyl 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl]acetate → ethyl 2-(4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)cyclohex-3-en-1-yl)acetate

Participants

Reaction Steps

The title compound was prepared following the method described in step 1 for the preparation of Example 1, using (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate and ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)acetate as the reactants. The product was obtained as a mixture of diasteromers in 42.7% yield. MS: m/e 737.65 (M+H)+, 2.939 min (method 8). 1H NMR (400 MHz, CHLOROFORM-d) δ 5.32 (br. s., 1H), 5.19 (d, J=5.8 Hz, 1H), 4.72 (d, J=1.8 Hz, 1H), 4.61 (d, J=1.5 Hz, 1H), 4.21-4.09 (m, 2H), 3.15-2.96 (m, 8H), 2.77-2.54 (m, 4H), 2.52-2.40 (m, 1H), 2.34-2.08 (m, 4H), 2.03-1.72 (m, 7H), 1.70 (s, 3H), 1.61-1.39 (m, 9H), 1.39-1.19 (m, 10H), 1.12-1.04 (m, 7H), 1.01-0.97 (m, 6H), 0.96-0.91 (m, 3H), 0.87 (s, 3H).

Provenance & Evidence