Technology Process of Methanesulfonic acid (S)-1-{2-[(8S,10R)-10-propyl-9-(toluene-4-sulfonyl)-1,5-dithia-9-aza-spiro[5.5]undec-8-yl]-ethyl}-pentyl ester
There total 12 articles about Methanesulfonic acid (S)-1-{2-[(8S,10R)-10-propyl-9-(toluene-4-sulfonyl)-1,5-dithia-9-aza-spiro[5.5]undec-8-yl]-ethyl}-pentyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: Zn(OTf)2; triethylamine; chiral 3-TBDMSO-2-(dimethylamino)-1-(4-nitrophenyl)propanol / toluene / 0.25 h / 20 °C
1.2: 83 percent / toluene / 12 h
2.1: 98 percent / 2,6-lutidine / CH2Cl2 / 1 h
3.1: 78 percent / m-CPBA / CH2Cl2 / 3.5 h / 20 °C
4.1: 92 percent / H2 / Pd/C / ethyl acetate / 2 h / 760 Torr
5.1: 49 percent / AcOH; H2O / chiral salen cobalt(II) complex / tetrahydrofuran / 0 - 20 °C
6.1: t-BuLi / diethyl ether / 1 h / -78 - -45 °C
6.2: diethyl ether / 5 h / -78 - -25 °C
6.3: 56 percent / hexamethylphosphoramide / diethyl ether / -78 - 0 °C
7.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 36 h / 20 °C
8.1: triethylamine / tetrahydrofuran / 0 - 20 °C
9.1: 0.058 g / K2CO3 / methanol / 3 h / 20 °C
With
2,6-dimethylpyridine; chiral 3-TBDMSO-2-(dimethylamino)-1-(4-nitrophenyl)propanol; tetrabutyl ammonium fluoride; water; hydrogen; tert.-butyl lithium; zinc trifluoromethanesulfonate; potassium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid;
palladium on activated charcoal; chiral salen cobalt(II);
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo052314g
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 98 percent / 2,6-lutidine / CH2Cl2 / 1 h
2.1: 78 percent / m-CPBA / CH2Cl2 / 3.5 h / 20 °C
3.1: 92 percent / H2 / Pd/C / ethyl acetate / 2 h / 760 Torr
4.1: 49 percent / AcOH; H2O / chiral salen cobalt(II) complex / tetrahydrofuran / 0 - 20 °C
5.1: t-BuLi / diethyl ether / 1 h / -78 - -45 °C
5.2: diethyl ether / 5 h / -78 - -25 °C
5.3: 56 percent / hexamethylphosphoramide / diethyl ether / -78 - 0 °C
6.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 36 h / 20 °C
7.1: triethylamine / tetrahydrofuran / 0 - 20 °C
8.1: 0.058 g / K2CO3 / methanol / 3 h / 20 °C
With
2,6-dimethylpyridine; tetrabutyl ammonium fluoride; water; hydrogen; tert.-butyl lithium; potassium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid;
palladium on activated charcoal; chiral salen cobalt(II);
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1021/jo052314g
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 49 percent / AcOH; H2O / chiral salen cobalt(II) complex / tetrahydrofuran / 0 - 20 °C
2.1: t-BuLi / diethyl ether / 1 h / -78 - -45 °C
2.2: diethyl ether / 5 h / -78 - -25 °C
2.3: 56 percent / hexamethylphosphoramide / diethyl ether / -78 - 0 °C
3.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 36 h / 20 °C
4.1: triethylamine / tetrahydrofuran / 0 - 20 °C
5.1: 0.058 g / K2CO3 / methanol / 3 h / 20 °C
With
tetrabutyl ammonium fluoride; water; tert.-butyl lithium; potassium carbonate; acetic acid; triethylamine;
chiral salen cobalt(II);
In
tetrahydrofuran; methanol; diethyl ether;
DOI:10.1021/jo052314g