Technology Process of (1S,6R)-6-(3,4-dichlorophenyl)-1-(4-methyl-1,3-thiazol-2-yl)-3-azabicyclo[4.1.0]heptane
There total 10 articles about (1S,6R)-6-(3,4-dichlorophenyl)-1-(4-methyl-1,3-thiazol-2-yl)-3-azabicyclo[4.1.0]heptane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: N-ethyl-N,N-diisopropylamine / toluene / 0.85 h / -7 - 1 °C
2.1: water; N-ethyl-N,N-diisopropylamine; triphenylphosphine / palladium diacetate / toluene / -5 - 70 °C
3.1: lithium tert-butoxide / 1-methyl-pyrrolidin-2-one; toluene
4.1: potassium tert-butylate; water / ethanol / 18 h / 50 °C
5.1: 1,1'-carbonyldiimidazole / ethyl acetate / 1.5 h / 20 °C
5.2: 18 h / 20 °C / Cooling with ice
6.1: Lawessons reagent / tetrahydrofuran / 4 h / 20 °C / Reflux
7.1: toluene / 80 °C / Reflux
8.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
9.1: chiral column Chiralcel OD-H, 25 x 0.46 cm / ethanol; hexane / Resolution of racemate
With
Lawessons reagent; potassium tert-butylate; water; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; lithium tert-butoxide;
palladium diacetate;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; hexane; dichloromethane; ethyl acetate; toluene;
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: triethylamine / n-heptane / 1.25 h / 20 °C
2.1: N-ethyl-N,N-diisopropylamine / toluene / 0.85 h / -7 - 1 °C
3.1: water; N-ethyl-N,N-diisopropylamine; triphenylphosphine / palladium diacetate / toluene / -5 - 70 °C
4.1: lithium tert-butoxide / 1-methyl-pyrrolidin-2-one; toluene
5.1: potassium tert-butylate; water / ethanol / 18 h / 50 °C
6.1: 1,1'-carbonyldiimidazole / ethyl acetate / 1.5 h / 20 °C
6.2: 18 h / 20 °C / Cooling with ice
7.1: Lawessons reagent / tetrahydrofuran / 4 h / 20 °C / Reflux
8.1: toluene / 80 °C / Reflux
9.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
10.1: chiral column Chiralcel OD-H, 25 x 0.46 cm / ethanol; hexane / Resolution of racemate
With
Lawessons reagent; potassium tert-butylate; water; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; lithium tert-butoxide;
palladium diacetate;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; hexane; n-heptane; dichloromethane; ethyl acetate; toluene;
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: water; N-ethyl-N,N-diisopropylamine; triphenylphosphine / palladium diacetate / toluene / -5 - 70 °C
2.1: lithium tert-butoxide / 1-methyl-pyrrolidin-2-one; toluene
3.1: potassium tert-butylate; water / ethanol / 18 h / 50 °C
4.1: 1,1'-carbonyldiimidazole / ethyl acetate / 1.5 h / 20 °C
4.2: 18 h / 20 °C / Cooling with ice
5.1: Lawessons reagent / tetrahydrofuran / 4 h / 20 °C / Reflux
6.1: toluene / 80 °C / Reflux
7.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
8.1: chiral column Chiralcel OD-H, 25 x 0.46 cm / ethanol; hexane / Resolution of racemate
With
Lawessons reagent; potassium tert-butylate; water; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; lithium tert-butoxide;
palladium diacetate;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; hexane; dichloromethane; ethyl acetate; toluene;
