Technology Process of [1R,4S,5S,6S,4(1'S)]-1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)propyl-1'-carbamic acid tert-butyl ester
There total 15 articles about [1R,4S,5S,6S,4(1'S)]-1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)propyl-1'-carbamic acid tert-butyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
methyllithium;
With
copper(I) bromide dimethylsulfide complex;
In
diethyl ether;
at 0 ℃;
[1R,4S,5S,6S,4(1'S)]-1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)aziridine-1-carboxylic acid tert-butyl ester;
In
diethyl ether; dichloromethane;
at 0 - 20 ℃;
for 0.166667h;
Further stages.;
DOI:10.1021/jo001257i
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: n-BuLi; 18-crown-6 / tetrahydrofuran; hexane / 1.17 h / -78 °C
1.2: 76 percent / tetrahydrofuran; hexane / 2.25 h / -78 °C
2.1: 87 percent / H2; ethylenediamine / P-2 Ni / ethanol
3.1: N,N-dimethylaniline / CH2Cl2 / 0.25 h / 0 °C
4.1: 516 mg / Et3N / CH2Cl2 / 0.42 h / 0 - 20 °C
5.1: Cu(TBS)2 / toluene / Heating
6.1: aq. HCl; triethylsilane / dioxane / 1 h
7.1: Et3N / acetonitrile / 12 h / 20 °C
8.1: 95 percent / DEAD; PPh3 / tetrahydrofuran / 3.5 h / 20 °C
9.1: CuBr*DMS / diethyl ether / 0 °C
9.2: 93 percent / diethyl ether; CH2Cl2 / 0.17 h / 0 - 20 °C
With
hydrogenchloride; triethylsilane; n-butyllithium; copper(I) bromide dimethylsulfide complex; 18-crown-6 ether; hydrogen; N,N-dimethyl-aniline; ethylenediamine; triethylamine; triphenylphosphine; diethylazodicarboxylate;
Cu(TBS)2;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile;
8.1: Mitsunobu cyclization;
DOI:10.1021/jo001257i
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 13 percent / ZnBr2 / diethyl ether / -78 - 20 °C
2.1: 87 percent / H2; ethylenediamine / P-2 Ni / ethanol
3.1: N,N-dimethylaniline / CH2Cl2 / 0.25 h / 0 °C
4.1: 516 mg / Et3N / CH2Cl2 / 0.42 h / 0 - 20 °C
5.1: Cu(TBS)2 / toluene / Heating
6.1: aq. HCl; triethylsilane / dioxane / 1 h
7.1: Et3N / acetonitrile / 12 h / 20 °C
8.1: 95 percent / DEAD; PPh3 / tetrahydrofuran / 3.5 h / 20 °C
9.1: CuBr*DMS / diethyl ether / 0 °C
9.2: 93 percent / diethyl ether; CH2Cl2 / 0.17 h / 0 - 20 °C
With
hydrogenchloride; triethylsilane; copper(I) bromide dimethylsulfide complex; hydrogen; N,N-dimethyl-aniline; ethylenediamine; triethylamine; triphenylphosphine; zinc dibromide; diethylazodicarboxylate;
Cu(TBS)2;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; toluene; acetonitrile;
8.1: Mitsunobu cyclization;
DOI:10.1021/jo001257i
