(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)-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 → methyl 1-cyano-4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)-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-enecarboxylate

Participants

Reaction Steps

The title compound was prepared following the procedure described in general procedure Step 5, using (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)-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 methyl 1-cyano-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enecarboxylate as reactants. The product was isolated as a mixture of diasteromers (solid, 61% yield). MS: m/e 762.6 (M+H)+, 3.01 min (method 4). 1H NMR (400 MHz, CHLOROFORM-d) δ 5.34 (d, J=2.0 Hz, 1H), 5.28-5.22 (m, 1H), 4.71 (d, J=2.0 Hz, 1H), 4.60-4.57 (m, 1H), 3.85 (s, 3H), 3.17-3.06 (m, 3H), 2.87-2.78 (m, 2H), 2.84 (s. 3H), 2.74-2.40 (m, 10H), 2.33-0.78 (m, 27H), 1.69 (s, 3H), 1.07 (s, 3H), 1.01-0.93 (m, 6H), 0.96 (s, 3H), 0.85 (s, 3H).

Provenance & Evidence