N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-trifluoromethanesulfonylmethanesulfonamide → (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-((2-(N-(5-chloropyridin-2-yl)-1,1,1-trifluoromethylsulfonamido)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

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

(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 (353 mg, 0.781 mmol) was mixed with N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide (338 mg, 0.860 mmol) in THF (2 mL) under nitrogen. The solution was stirred at −78° C. under nitrogen. A 0.5 M stock solution of potassium bis(trimethylsilyl)amide (1.875 mL, 0.938 mmol) was added, and the mixture was stirred at −78° C. for an hour. The desired product was purified by silica gel chromatography eluted with mixture of ethyl acetate and hexanes (230 mg, 35%). MS: m/e 844.3/846.3 (M+H)+, 6.47 min (method 15). 1H NMR (400 MHz, CHLOROFORM-d) δ (key fingerprint signals) 8.45 (d, J=2.0 Hz, 1H), 7.76 (dd, J=8.7, 2.6 Hz, 1H), 7.48 (d, J=8.5 Hz, 1H), 5.57 (d, J=6.5 Hz, 1H), 4.80-4.57 (m, 3H), 3.71-3.65 (m, 1H), 2.80-2.73 (m, 1H), 2.73-2.49 (m, 2H), 2.45-2.29 (m, 1H), 2.26-2.12 (m, 2H), 2.08-1.94 (m, 2H), 1.93-1.80 (m, 2H), 1.80-1.72 (m, 3H), 1.71-1.65 (m, 6H). 19F NMR (376 MHz, CHLOROFORM-d) δ −74.84 (s), −74.85 (s).

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