Technology Process of 3-Pyrrolidinecarboxylicacid, 4-hydroxy-1-[2-(4-hydroxyphenyl)ethyl]-5-(2-oxooctadecylidene)-2-propyl-,methyl ester, (2S,3S,4R,5E)-
There total 15 articles about 3-Pyrrolidinecarboxylicacid, 4-hydroxy-1-[2-(4-hydroxyphenyl)ethyl]-5-(2-oxooctadecylidene)-2-propyl-,methyl ester, (2S,3S,4R,5E)- which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 13 steps
1.1: DCC; HOBt
2.1: LAH
3.1: 82 percent / n-BuLi
4.1: 51 percent / LDA
5.1: H2 / Pd/C
5.2: ethyl acetate / reflux
6.1: DMAP
7.1: P4S10; NaHCO3
8.1: TsOH / methanol
9.1: Et3N
10.1: 90 percent / K2CO3 / methanol / 0.5 h
11.1: CH2Cl2
12.1: PPh3; Et3N
13.1: 71 percent / n-Bu4NF; AcOH / tetrahydrofuran
With
dmap; lithium aluminium tetrahydride; n-butyllithium; tetraphosphorus decasulfide; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane;
1.1: Acylation / 2.1: Reduction / 3.1: Addition / 4.1: Addition / 4.2: Addition / 5.1: Hydrogenolysis / 5.2: Cyclization / 6.1: silylation / 7.1: sulfuration / 8.1: desilylation / 9.1: silylation / 10.1: Isomerization / 11.1: Alkylation / 12.1: Alkylation / 13.1: desylilation;
DOI:10.1016/S0040-4039(00)00096-4
- Guidance literature:
-
Multi-step reaction with 15 steps
1.1: K2CO3 / dimethylformamide
2.1: NaOH / H2O; methanol
3.1: DCC; HOBt
4.1: LAH
5.1: 82 percent / n-BuLi
6.1: 51 percent / LDA
7.1: H2 / Pd/C
7.2: ethyl acetate / reflux
8.1: DMAP
9.1: P4S10; NaHCO3
10.1: TsOH / methanol
11.1: Et3N
12.1: 90 percent / K2CO3 / methanol / 0.5 h
13.1: CH2Cl2
14.1: PPh3; Et3N
15.1: 71 percent / n-Bu4NF; AcOH / tetrahydrofuran
With
dmap; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; tetraphosphorus decasulfide; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
1.1: Etherification / 2.1: Hydrolysis / 3.1: Acylation / 4.1: Reduction / 5.1: Addition / 6.1: Addition / 6.2: Addition / 7.1: Hydrogenolysis / 7.2: Cyclization / 8.1: silylation / 9.1: sulfuration / 10.1: desilylation / 11.1: silylation / 12.1: Isomerization / 13.1: Alkylation / 14.1: Alkylation / 15.1: desylilation;
DOI:10.1016/S0040-4039(00)00096-4