Acetic Acid → ethyl 4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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

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Reaction Steps

To a solution of ethyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-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-enecarboxylate (0.1 g, 0.178 mmol) in ethanol (5 mL), 1,4-dioxane (2 mL) and acetic acid (0.051 mL, 0.890 mmol) was added 10% palladium on carbon (0.095 g, 0.089 mmol). The mixture was evacuated and refilled with nitrogen three times then was stirred under 1 atmosphere of hydrogen gas for 16 h. The mixture was evacuated and flushed with nitrogen, then was filtered through celite and was concentrated under reduced pressure to give the expected product (0.100 g, 0.178 mmol, 100% yield) as an off-white solid. 1H NMR (400 MHz, chloroform-d) δ=5.36 (br. s., 1H), 5.19 (d, J=5.8 Hz, 1H), 4.19-4.11 (m, 2H), 2.57-2.47 (m, 1H), 2.31 (dd, J=2.9, 2.1 Hz, 2H), 2.17 (dd, J=4.6, 2.6 Hz, 2H), 2.12-0.70 (m, 52H).

Provenance & Evidence