4-(Methanesulfonyl)piperidine → ethyl 3-((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)bicyclo[3.1.0]hex-2-ene-6-carboxylate

Beteiligte Stoffe

Reaktionsschritte

The title compound was prepared following the method describe on step 1 for the preparation of (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-(aziridin-1-yl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)octadecahydro-1H-cyclopenta[a]chrysen-9(5bH)-one using 4-(methylsulfonyl)piperidine and ethyl 3-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(aziridin-1-yl)-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)bicyclo[3.1.0]hex-2-ene-6-carboxylate as the reactants. The product was obtained as a mixture of diastereomers in 33.2% yield. MS: m/e 749.6 (M+H)+, 2.794 min (method 8). 1H NMR (400 MHz, CHLOROFORM-d) δ 5.84-5.75 (m, 1H), 5.49-5.38 (m, 1H), 4.69 (br. s., 1H), 4.59 (br. s., 1H), 4.19-4.04 (m, 2H), 3.12 (dd, J=15.6, 12.8 Hz, 1H), 2.98-2.74 (m, 7H), 2.68-2.51 (m, 5H), 2.45 (d, J=7.5 Hz, 4H), 2.22-2.10 (m, 3H), 2.09-1.74 (m, 8H), 1.69 (s, 3H), 1.65-1.30 (m, 12H), 1.26 (m, 6H), 1.06 (br. s., 5.5H), 1.02 (s, 3H), 0.98-0.92 (m, 4.5H), 0.85-0.78 (m, 3H).

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