反应详情

温度

100 °C

tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(aminomethyl)-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)benzoate (200 mg, 0.667 mmol) was dissolved in DMF (10.00 mL) and THF (10.00 mL), ethane-1,2-diylbis(4-methylbenzenesulfonate) (247 mg, 0.667 mmol) was added, followed by K2CO3 (184 mg, 1.333 mmol) and the mixture was stirred at 100° C. until no starting material was detected by LCMS. An M+1=626.7 was observed by LC-MS. The reaction mixture was redissolved in CH2Cl2 (100 mL), washed by water (2×50 mL) and the organic layer was dried over sodium sulfate. The solvent was removed in vacuo and the resultant residue was purified by silica gel chromatography using a mixture of ethyl acetate/hexanes. A white foam was obtained (130 mg, 65%) LCMS: m/e 426.7 (MH+), 4.393 min (method 8). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.90 (d, J=8.3 Hz, 2H), 7.24-7.11 (m, 2H), 5.30 (d, J=1.8 Hz, 1H), 4.70 (d, J=2.0 Hz, 1H), 4.60 (dd, J=2.3, 1.3 Hz, 1H), 2.56 (d, J=21.1 Hz, 1H), 2.44-2.33 (m, 1H), 2.26-2.05 (m, 3H), 2.04-1.89 (m, 1H), 1.86 (d, J=12.0 Hz, 1H), 1.82-1.58 (m, 18H), 1.56-1.37 (m, 7H), 1.35-1.21 (m, 6H), 1.19-1.06 (m, 6H), 1.03 (s, 3H), 0.99 (s, 3H), 0.93 (m, 6H)

1. washwashed by water (2×50 mL)
2. dry with materialthe organic layer was dried over sodium sulfate
3. customThe solvent was removed in vacuo
4. customthe resultant residue was purified by silica gel chromatography
5. additiona mixture of ethyl acetate/hexanes
6. customA white foam was obtained (130 mg, 65%) LCMS
7. customm/e 426.7 (MH+), 4.393 min (method 8)