Technology Process of 1-Pyrrolidinecarboxylic acid,
2-[(1R,2S)-2-methoxy-2-methyl-1-[[(triphenylmethyl)thio]amino]pentyl]-5-
oxo-3-(1Z)-1-propenyl-, 1,1-dimethylethyl ester, (2R,3S)-
There total 18 articles about 1-Pyrrolidinecarboxylic acid,
2-[(1R,2S)-2-methoxy-2-methyl-1-[[(triphenylmethyl)thio]amino]pentyl]-5-
oxo-3-(1Z)-1-propenyl-, 1,1-dimethylethyl ester, (2R,3S)- which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
(Z)-1-propenylmagnesium bromide;
With
chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex;
In
tetrahydrofuran;
at -30 - -20 ℃;
for 0.5h;
tert-butyl (2R)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(triphenylmethylsulfenyl)amino]pentyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate;
In
tetrahydrofuran; toluene;
at -20 ℃;
for 0.416667h;
DOI:10.1016/S0957-4166(03)00597-4
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: (-)-dimethyl D-tartrate; titanium tetraisopropoxide; tert-butylhydroperoxide / molecular sieves 4 Angstroem / CH2Cl2; decane / 4 h / -20 °C
2.1: 7.35 g / trimethylphosphite; triethylamine / CH2Cl2; decane / 1.5 h
3.1: 63 percent / lithium aluminum hydride / tetrahydrofuran / 0 - 20 °C
4.1: 98 percent / sodium hydride / tetrahydrofuran / 16 h / 0 - 20 °C
5.1: 98 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 16 h / 0 - 20 °C
6.1: hydrogen / 20percent Pd(OH)2 on carbon / CH2Cl2 / 3.5 h
7.1: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH2Cl2 / 1.5 h / 20 °C
8.1: pyridinium p-toluenesulfonate; MgSO4 / diethyl ether / 18 h / 20 °C
9.1: 52 percent / BF3*Et2O / diethyl ether / 3 h / -78 - -50 °C
10.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating
10.2: CuBr*Me2S; trimethylsilylchloride / tetrahydrofuran / 1.67 h / -78 °C
10.3: 6.9 g / tetrahydrofuran / 1 h / -78 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; Dimethyl D-tartrate; 4 A molecular sieve; Celite; boron trifluoride diethyl etherate; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; magnesium sulfate; magnesium; ethylene dibromide; triethylamine; pyridinium chlorochromate; phosphorous acid trimethyl ester;
4 A molecular sieve;
In
tetrahydrofuran; diethyl ether; decane; dichloromethane;
10.3: Michael addition;
DOI:10.1021/jo0162890
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 80 percent / lithium aluminum hydride / diethyl ether / 2 h / 0 - 20 °C
2.1: (-)-dimethyl D-tartrate; titanium tetraisopropoxide; tert-butylhydroperoxide / molecular sieves 4 Angstroem / CH2Cl2; decane / 4 h / -20 °C
3.1: 7.35 g / trimethylphosphite; triethylamine / CH2Cl2; decane / 1.5 h
4.1: 63 percent / lithium aluminum hydride / tetrahydrofuran / 0 - 20 °C
5.1: 98 percent / sodium hydride / tetrahydrofuran / 16 h / 0 - 20 °C
6.1: 98 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 16 h / 0 - 20 °C
7.1: hydrogen / 20percent Pd(OH)2 on carbon / CH2Cl2 / 3.5 h
8.1: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH2Cl2 / 1.5 h / 20 °C
9.1: pyridinium p-toluenesulfonate; MgSO4 / diethyl ether / 18 h / 20 °C
10.1: 52 percent / BF3*Et2O / diethyl ether / 3 h / -78 - -50 °C
11.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating
11.2: CuBr*Me2S; trimethylsilylchloride / tetrahydrofuran / 1.67 h / -78 °C
11.3: 6.9 g / tetrahydrofuran / 1 h / -78 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; Dimethyl D-tartrate; 4 A molecular sieve; Celite; boron trifluoride diethyl etherate; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; magnesium sulfate; magnesium; ethylene dibromide; triethylamine; pyridinium chlorochromate; phosphorous acid trimethyl ester;
4 A molecular sieve;
In
tetrahydrofuran; diethyl ether; decane; dichloromethane;
11.3: Michael addition;
DOI:10.1021/jo0162890
