Technology Process of 3-[N-(methoxycarbonyl)methyl]-7-hydroxy-9-benzyloxy-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoline
There total 13 articles about 3-[N-(methoxycarbonyl)methyl]-7-hydroxy-9-benzyloxy-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoline 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:
-
With
potassium hydrogencarbonate;
In
tetrahydrofuran;
at 0 - 20 ℃;
for 3h;
DOI:10.1021/jo991162k
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 76 percent / triethylamine / CH2Cl2 / 2 h / -78 °C
2.1: m-CPBA / CH2Cl2 / 18 h / 20 °C
3.1: 73 percent / tin tetrachloride / CH2Cl2 / 3.5 h / -20 - 0 °C
4.1: 28.1 g / tri-tert-butylphosphine / tetrahydrofuran / 1 h / 20 °C
5.1: 12.0 g / m-CPBA; aq. NaHCO3 / CH2Cl2 / 1.08 h / 0 - 20 °C
6.1: OsO4 / dioxane; H2O / 0.08 h / 20 °C
6.2: 53 percent / NaIO4 / dioxane; H2O / 3 h / 20 °C
7.1: 100 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C
8.1: BBr3 / CH2Cl2 / 4.5 h / -78 - 20 °C
9.1: K2CO3 / dimethylsulfoxide / 20 h / 20 °C
10.1: 92 percent / LiAlH4 / tetrahydrofuran; toluene / 4 h / Heating
11.1: KHCO3 / tetrahydrofuran / 3 h / 0 - 20 °C
With
osmium(VIII) oxide; lithium aluminium tetrahydride; tri-tert-butyl phosphine; boron tribromide; tin(IV) chloride; sodium hydrogencarbonate; potassium carbonate; potassium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene;
1.1: Addition / 2.1: Epoxidation / 3.1: Cyclization / 4.1: Substitution / 5.1: Oxidation / 6.1: Oxidation / 6.2: Oxidation / 7.1: Reduction / 8.1: demethylation / 9.1: Alkylation / 10.1: Reduction / 11.1: Alkylation;
DOI:10.1021/jo991162k
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 31.6 g / sodium cyanoborohydride / acetic acid / 2 h / 20 °C
2.1: 76 percent / triethylamine / CH2Cl2 / 2 h / -78 °C
3.1: m-CPBA / CH2Cl2 / 18 h / 20 °C
4.1: 73 percent / tin tetrachloride / CH2Cl2 / 3.5 h / -20 - 0 °C
5.1: 28.1 g / tri-tert-butylphosphine / tetrahydrofuran / 1 h / 20 °C
6.1: 12.0 g / m-CPBA; aq. NaHCO3 / CH2Cl2 / 1.08 h / 0 - 20 °C
7.1: OsO4 / dioxane; H2O / 0.08 h / 20 °C
7.2: 53 percent / NaIO4 / dioxane; H2O / 3 h / 20 °C
8.1: 100 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C
9.1: BBr3 / CH2Cl2 / 4.5 h / -78 - 20 °C
10.1: K2CO3 / dimethylsulfoxide / 20 h / 20 °C
11.1: 92 percent / LiAlH4 / tetrahydrofuran; toluene / 4 h / Heating
12.1: KHCO3 / tetrahydrofuran / 3 h / 0 - 20 °C
With
osmium(VIII) oxide; lithium aluminium tetrahydride; tri-tert-butyl phosphine; boron tribromide; tin(IV) chloride; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; potassium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; acetic acid; dimethyl sulfoxide; toluene;
1.1: Reduction / 2.1: Addition / 3.1: Epoxidation / 4.1: Cyclization / 5.1: Substitution / 6.1: Oxidation / 7.1: Oxidation / 7.2: Oxidation / 8.1: Reduction / 9.1: demethylation / 10.1: Alkylation / 11.1: Reduction / 12.1: Alkylation;
DOI:10.1021/jo991162k
