Technology Process of (3aR,6aR)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester
There total 12 articles about (3aR,6aR)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester 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:
-
(3aR,6aR)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester;
With
trifluoroacetic acid;
In
dichloromethane;
at 0 ℃;
for 2h;
With
sodium hydrogencarbonate;
In
water; ethyl acetate;
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C
2.1: pyridine-SO3 complex; triethylamine / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 20 °C
3.1: triethylamine / 12 h
3.2: 1 h / -78 °C
3.3: 1 h / -78 °C
4.1: silica gel; sodium iodide / cerium(III) chloride heptahydrate / acetonitrile / 0.5 h / 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 0 °C
6.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 1 h / 0 °C
7.1: hydrogen / palladium 10% on activated carbon / ethanol / 16 h / 2844.39 Torr
8.1: sodium acetate / ethanol / 3 h / Reflux
9.1: dichloromethane / 2 h / 0 °C
10.1: trifluoroacetic acid / dichloromethane / 2 h / 0 °C
With
lithium borohydride; pyridine-SO3 complex; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; silica gel; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium iodide;
dmap; cerium(III) chloride heptahydrate; palladium 10% on activated carbon;
In
tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile;
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: triethylamine / 12 h
1.2: 1 h / -78 °C
1.3: 1 h / -78 °C
2.1: silica gel; sodium iodide / cerium(III) chloride heptahydrate / acetonitrile / 0.5 h / 20 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 0 °C
4.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 1 h / 0 °C
5.1: hydrogen / palladium 10% on activated carbon / ethanol / 16 h / 2844.39 Torr
6.1: sodium acetate / ethanol / 3 h / Reflux
7.1: dichloromethane / 2 h / 0 °C
8.1: trifluoroacetic acid / dichloromethane / 2 h / 0 °C
With
tetrabutyl ammonium fluoride; hydrogen; sodium acetate; silica gel; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium iodide;
dmap; cerium(III) chloride heptahydrate; palladium 10% on activated carbon;
In
tetrahydrofuran; ethanol; dichloromethane; acetonitrile;