DeacetylniMbinene synthesis
- Product Name:DeacetylniMbinene
- CAS Number:78916-55-9
- Molecular formula:C11H8ClN3OS2
- Molecular Weight:297.7837
25990-37-8
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Yield:78916-55-9 64%
Reaction Conditions:
with lithium hydroxyde monohydrate in tetrahydrofuran at 70; for 7 h;Inert atmosphere;
Steps:
2.B.B 6-Deacetylnimbinene (S-61)
Under Ar (g), the nimbolide (26.8 mg, 0.057 mmol) and LiOH-H20 (4.8 mg, 0.0857 mmol, 2.0 eq) were dissolved in 2 ml THF and stirred at 70 °C for 7 hours. Then remove the solvent via rotary evaporation to give the crude. Purification on the silica gel chromatography (S1O2, hexane : EA = 5 : 1) afforded the 6-deacetylnimbinene (S-61) as colorless oil (16.3 mg, 64%). (0668) [a] D24 = + 124.45 (c 0.143, CHCb), (literature [a] D20 = + 132 (c 1, CHCb). 4H NMR (600 MHz, CDCb): d 7.30 (t, / = 1.7 Hz, 1H), 7.20 (s, 1H), 6.27 (t, /= 1.3 Hz, 1H), 5.56 (s, 1H), 5.44 (ddt, /= 8.5, 6.6, 2.0 Hz, 1H), 4.02 (q, /= 8.6, 6.0 Hz, 2H), 3.65 (d, /= 7.8 Hz, 1H), 3.57 (s, 3H), 2.96 (ddq, /= 19.3, 5.4, 2.9 Hz, 1H), 2.87 (dd, /= 19.3, 5.7 Hz, 1H), 2.83 - 2.76 (m, 2H), 2.64 (dd, / = 6.1, 4.4 Hz, 1H), 2.35 - 2.26 (m, 1H), 2.25 - 2.19 (m, 1H), 2.16 (dd, J = 11.8, 6.5 Hz, 1H), 2.07 - 1.99 (m, 4H), 1.68 (d, J = 1.9 Hz, 3H), 1.31 (s, 3H), 1.04 (s, 3H) ppm. 13C NMR (150 MHz, CDCb): 5213.27, 173.71, 147.31, 143.15, 138.98, 138.69, 134.91, 126.85, 119.19, 110.44, 88.02, 86.43, 66.44, 51.71, 49.57, 49.44, 47.33, 47.30, 41.38, 40.01, 37.19, 33.69, 21.81, 17.49, 14.08, 12.94 ppm. HRMS (ESI-TOF): calc’d for C26H32O6 [M+H]+: 463.2091, found: 463.2081. TLC: R/= 0.65 (1:1 hexanes : ethyl acetate).
References:
WO2022/150667,2022,A1 Location in patent:Page/Page column 200-201
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