Technology Process of (1R,3S)-4-Methylene-5-[2-[(1R,7aR)-7a-methyl-1-((1S,2R)-7,7,7-trifluoro-2,6-dihydroxy-1-methyl-6-trifluoromethyl-heptyl)-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexane-1,3-diol
There total 32 articles about (1R,3S)-4-Methylene-5-[2-[(1R,7aR)-7a-methyl-1-((1S,2R)-7,7,7-trifluoro-2,6-dihydroxy-1-methyl-6-trifluoromethyl-heptyl)-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexane-1,3-diol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 39 percent / diethyl ether; tetrahydrofuran / 0 °C
2: pyridine / Ambient temperature
3: 35 h / 150 °C
4: K2CO3 / methanol / Ambient temperature
5: Collins reagent
6: 96 percent / H2 / 5percent Pd/C / methanol / 1 h / 760 Torr / Ambient temperature
7: 67 percent / NaBH4 / ethanol / Ambient temperature
8: 2,6-lutidine / CH2Cl2 / Ambient temperature
9: H2 / 5percent Pd/C / methanol / 760 Torr / Ambient temperature
10: pyridinium chlorochromate
11: 1.) n-BuLi / 1.) THF, from -78 deg C to TR, 2.) THF
12: n-Bu4N(1+)*F(1-) / tetrahydrofuran / 60 °C
With
pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; Collins oxidation agent; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; pyridinium chlorochromate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;
DOI:10.1248/cpb.40.1346
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 39 percent / diethyl ether; tetrahydrofuran / 0 °C
2: pyridine / Ambient temperature
3: 35 h / 150 °C
4: K2CO3 / methanol / Ambient temperature
5: Collins reagent
6: 96 percent / H2 / 5percent Pd/C / methanol / 1 h / 760 Torr / Ambient temperature
7: 23 percent / NaBH4 / ethanol / Ambient temperature
8: 2,6-lutidine / CH2Cl2 / Ambient temperature
9: H2 / 5percent Pd/C / methanol / 760 Torr / Ambient temperature
10: pyridinium chlorochromate
11: 1.) n-BuLi / 1.) THF, from -78 deg C to RT, 2.) THF
12: n-Bu4N(1+)*F(1-) / tetrahydrofuran / 60 °C
With
pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; Collins oxidation agent; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; pyridinium chlorochromate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;
DOI:10.1248/cpb.40.1346
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 95 percent / pyridine / Ambient temperature
2: 74 percent / 35 h / 150 °C
3: 92 percent / K2CO3 / methanol / Ambient temperature
4: 96 percent / Collins reagent
5: 96 percent / H2 / 5percent Pd/C / methanol / 1 h / 760 Torr / Ambient temperature
6: 67 percent / NaBH4 / ethanol / Ambient temperature
7: 2,6-lutidine / CH2Cl2 / Ambient temperature
8: H2 / 5percent Pd/C / methanol / 760 Torr / Ambient temperature
9: pyridinium chlorochromate
10: 1.) n-BuLi / 1.) THF, from -78 deg C to TR, 2.) THF
11: n-Bu4N(1+)*F(1-) / tetrahydrofuran / 60 °C
With
pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; Collins oxidation agent; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; pyridinium chlorochromate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1248/cpb.40.1346
