Technology Process of 1,2-Pyrrolidinedicarboxylic acid,
2-[(1S,3S,5S,6S,8R)-8-(benzoyloxy)-1-(1,1-dimethylethyl)-5-hydroxy-3,
6-dimethyl-7-oxononyl] 1-(1,1-dimethylethyl) ester, (2S)-
There total 8 articles about 1,2-Pyrrolidinedicarboxylic acid,
2-[(1S,3S,5S,6S,8R)-8-(benzoyloxy)-1-(1,1-dimethylethyl)-5-hydroxy-3,
6-dimethyl-7-oxononyl] 1-(1,1-dimethylethyl) ester, (2S)- 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:
-
(-)-(R)-3-oxopentan-2-yl benzoate;
With
N,N-dimethyl-ethanamine; dicyclohexylboron chloride;
In
diethyl ether;
at 0 ℃;
for 1.5h;
pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-(1-tert-butyl-3-methyl-5-oxo-pentyl) ester;
In
diethyl ether;
at -78 - -20 ℃;
for 19h;
With
dihydrogen peroxide;
In
methanol;
at 20 ℃;
for 3h;
DOI:10.1021/ja036050w
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: diisopropylethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 20 °C
1.2: 94 percent / N,N-dimethyl-4-aminopyridine / toluene / 3 h / 20 °C
2.1: 88 percent / tetra-N-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C
3.1: 4 Angstroem molecular sieves; N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate / CH2Cl2 / 0.5 h / 20 °C
4.1: dicyclohexylboron chloride; Me2NEt / diethyl ether / 1.5 h / 0 °C
4.2: diethyl ether / 19 h / -78 - -20 °C
4.3: aq. H2O2 / methanol / 3 h / 20 °C
With
tetrapropylammonium perruthennate; N,N-dimethyl-ethanamine; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja036050w
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 71 percent / Et3N; N-methyl-2-chloropyridinium iodide / CH2Cl2 / 2.5 h / Heating
2.1: titanium tetra-isopropoxide / CH2Cl2 / 1 h / 40 °C
2.2: 97 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / CH2Cl2 / 3 h / Heating
3.1: CuCN / diethyl ether / -78 - 0 °C
3.2: 86 percent / diethyl ether / 1 h / -78 - -25 °C
4.1: 83 percent / LiAlH4 / diethyl ether / 0.67 h / 0 °C
5.1: 86 percent / imidazole / CH2Cl2 / 0.5 h / 20 °C
6.1: diisopropylethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 20 °C
6.2: 94 percent / N,N-dimethyl-4-aminopyridine / toluene / 3 h / 20 °C
7.1: 88 percent / tetra-N-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C
8.1: 4 Angstroem molecular sieves; N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate / CH2Cl2 / 0.5 h / 20 °C
9.1: dicyclohexylboron chloride; Me2NEt / diethyl ether / 1.5 h / 0 °C
9.2: diethyl ether / 19 h / -78 - -20 °C
9.3: aq. H2O2 / methanol / 3 h / 20 °C
With
1H-imidazole; titanium(IV) isopropylate; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; N,N-dimethyl-ethanamine; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja036050w
