Technology Process of Benzoic acid (1S,3aS,3bS,8S,10aR,10bS,12aS)-10a,12a-dimethyl-6-oxo-8-(toluene-4-sulfonyloxy)-hexadecahydro-6a-aza-benzo[3,4]cyclohepta[1,2-e]inden-1-yl ester
There total 9 articles about Benzoic acid (1S,3aS,3bS,8S,10aR,10bS,12aS)-10a,12a-dimethyl-6-oxo-8-(toluene-4-sulfonyloxy)-hexadecahydro-6a-aza-benzo[3,4]cyclohepta[1,2-e]inden-1-yl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 4-(N,N-dimethylamino)pyridine, pyridine / 12 h / Ambient temperature
2: H2, quinoline / 5percent Pd/CaCO3/Pb / aq. ethanol / 760 Torr
3: 81 percent / NH2OH*HCl, pyridine / methanol / Heating
4: 45 percent / p-TsCl, 4-(N,N-dimethylamino)pyridine, pyridine / 65 °C
5: 96 percent / MCPBA / CHCl3
6: 1) NaI, 2) imidazole / 1) THF, 2 h, 2) DMF, 48 h
7: 1) NaH, 2) AcOH / 1) mineral oil, THF, r.t., 3 h, 2) mineral oil, THF, 0 deg C
8: 100 percent / n-Bu4NF / tetrahydrofuran
9: 94 percent / pyridine
With
pyridine; 1H-imidazole; quinoline; dmap; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; acetic acid; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; sodium iodide;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; ethanol; chloroform;
DOI:10.1021/jo00041a013
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 4-(N,N-dimethylamino)pyridine, pyridine / 12 h / Ambient temperature
2: H2, quinoline / 5percent Pd/CaCO3/Pb / aq. ethanol / 760 Torr
3: 81 percent / NH2OH*HCl, pyridine / methanol / Heating
4: 45 percent / p-TsCl, 4-(N,N-dimethylamino)pyridine, pyridine / 65 °C
5: 96 percent / MCPBA / CHCl3
6: 1) NaI, 2) imidazole / 1) THF, 2 h, 2) DMF, 48 h
7: 1) NaH, 2) AcOH / 1) mineral oil, THF, r.t., 3 h, 2) mineral oil, THF, 0 deg C
8: 100 percent / n-Bu4NF / tetrahydrofuran
9: 94 percent / pyridine
With
pyridine; 1H-imidazole; quinoline; dmap; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; acetic acid; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; sodium iodide;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; ethanol; chloroform;
DOI:10.1021/jo00041a013
- Guidance literature:
-
Multi-step reaction with 8 steps
1: H2, quinoline / 5percent Pd/CaCO3/Pb / aq. ethanol / 760 Torr
2: 81 percent / NH2OH*HCl, pyridine / methanol / Heating
3: 45 percent / p-TsCl, 4-(N,N-dimethylamino)pyridine, pyridine / 65 °C
4: 96 percent / MCPBA / CHCl3
5: 1) NaI, 2) imidazole / 1) THF, 2 h, 2) DMF, 48 h
6: 1) NaH, 2) AcOH / 1) mineral oil, THF, r.t., 3 h, 2) mineral oil, THF, 0 deg C
7: 100 percent / n-Bu4NF / tetrahydrofuran
8: 94 percent / pyridine
With
pyridine; 1H-imidazole; quinoline; dmap; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; acetic acid; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; sodium iodide;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; ethanol; chloroform;
DOI:10.1021/jo00041a013
