[1R-[1alpha(S*),3abeta,7aalpha]]-1-[2-(Acetyloxy)-1-methylethyl]octahydro-7a-methyl-4H-inden-4-one synthesis
- Product Name:[1R-[1alpha(S*),3abeta,7aalpha]]-1-[2-(Acetyloxy)-1-methylethyl]octahydro-7a-methyl-4H-inden-4-one
- CAS Number:141411-00-9
- Molecular formula:C15H24O3
- Molecular Weight:252.35
141245-56-9
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141411-00-9
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Yield:141411-00-9 87%
Reaction Conditions:
with dipyridinium dichromate in dichloromethane at 0; for 2.5 h;
Steps:
1
(20S)-Des-A,B-22-(acetoxy)-23,24-dinorcholane-8-one (3)To a stirred solution of 2 (64 mg; 0.25 mmol) and pyridiniump-toluenesulfonate (10 mg; 0.04 mmol) in methylene chloride (12 ml) pyridinium dichromate (244 mg; 0.65 mmol) was added at 0° C. The cooling bath was then removed and the reaction mixture was stirred for 2.5 hours. After that solvent was removed under reduced pressure and the residue was purified on silica gel Sep-Pack cartridge (15-25% ethyl acetate/hexane) to give 55 mg (0.22 mmol; 87% yield) of 3. 1H NMR (400 MHz, CDCl3) δ 0.66 (3H, s), 1.06 (3H, d, J=6.6 Hz), 2.47 (1H, dd, J=11.5 Hz, J=7.6 Hz), 3.82 (1H, dd, J=10.7 Hz, J=7.2 Hz), 4.08 (1H, dd, J=10.7 Hz, J=3.3 Hz); 13C NMR (101 MHz, CDCl3) δ 12.5, 17.2, 19.2, 21.0, 24.0, 27.0, 35.5, 38.8, 40.9, 49.9, 53.3, 61.6, 69.1, 171.3, 211.6; MS (EI) m/z 252 (M+, 18) 237 (18), 220 (24), 205 (64) 192 (80), 124 (100); exact mass (ESI) calculated for C15H21O3Na ([M+Na]+) 275.1623. found 275.1631.
References:
US2012/309719,2012,A1 Location in patent:Page/Page column 13-14
64190-52-9
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64190-52-9
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