Technology Process of 3,3-[1,2-ethanediylbis(oxy)]-11β-{4-{1,1-[1,2-ethanediylbis(oxy)]ethyl}phenyl}-5α-hydroxy-17α-(3-hydroxypropyl)-19-norpregn-9-en-20-one
There total 8 articles about 3,3-[1,2-ethanediylbis(oxy)]-11β-{4-{1,1-[1,2-ethanediylbis(oxy)]ethyl}phenyl}-5α-hydroxy-17α-(3-hydroxypropyl)-19-norpregn-9-en-20-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)magnesium bromide;
With
copper(I) bromide dimethylsulfide complex;
In
tetrahydrofuran;
at 20 ℃;
3,3-[1,2-ethanediylbis(oxy)]-17α-(3-hydroxypropyl)-5,10-oxido-19-norpregn-9-en-20-one;
In
tetrahydrofuran;
at 20 ℃;
Further stages.;
DOI:10.5555/ol007067b
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: LiCN / tetrahydrofuran; dimethylformamide / 0.5 h / 20 °C
1.2: 79 percent / SmI2 / tetrahydrofuran; 2-methyl-propan-2-ol / 3.5 h
2.1: LiNEt2 / tetrahydrofuran / 0.5 h / -78 °C
2.2: 73 percent / tetrahydrofuran / 0.17 h / -78 °C
3.1: 78 percent / DIBAL-H / toluene; various solvent(s) / 1.25 h / -42 °C
4.1: tetrahydrofuran; diethyl ether / -78 - 20 °C
5.1: 72 percent / DMSO; (COCl)2 / CH2Cl2 / -60 - 20 °C
6.1: disiamylborane / tetrahydrofuran / 20 °C
6.2: 83 percent / NaOH; H2O2 / tetrahydrofuran; H2O / -5 - 20 °C
7.1: 89 percent / H2O2; hexafluoroacetone; Na2HPO4 / CH2Cl2; H2O / 72 h
8.1: CuBr*SMe2 / tetrahydrofuran / 20 °C
8.2: 15 percent / tetrahydrofuran / 20 °C
With
disodium hydrogenphosphate; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; lithium cyanide; lithium diethylamide; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; dimethyl sulfoxide; Hexafluoroacetone;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;
5.1: Swern oxidation;
DOI:10.5555/ol007067b
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: LiNEt2 / tetrahydrofuran / 0.5 h / -78 °C
1.2: 73 percent / tetrahydrofuran / 0.17 h / -78 °C
2.1: 78 percent / DIBAL-H / toluene; various solvent(s) / 1.25 h / -42 °C
3.1: tetrahydrofuran; diethyl ether / -78 - 20 °C
4.1: 72 percent / DMSO; (COCl)2 / CH2Cl2 / -60 - 20 °C
5.1: disiamylborane / tetrahydrofuran / 20 °C
5.2: 83 percent / NaOH; H2O2 / tetrahydrofuran; H2O / -5 - 20 °C
6.1: 89 percent / H2O2; hexafluoroacetone; Na2HPO4 / CH2Cl2; H2O / 72 h
7.1: CuBr*SMe2 / tetrahydrofuran / 20 °C
7.2: 15 percent / tetrahydrofuran / 20 °C
With
disodium hydrogenphosphate; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; lithium diethylamide; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; dimethyl sulfoxide; Hexafluoroacetone;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;
4.1: Swern oxidation;
DOI:10.5555/ol007067b
