Technology Process of Acetic acid (1R,9S,9aS)-9-benzyloxymethyl-5,7-dimethoxy-6-methyl-1-phenylselanyl-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indol-8-yl ester
There total 10 articles about Acetic acid (1R,9S,9aS)-9-benzyloxymethyl-5,7-dimethoxy-6-methyl-1-phenylselanyl-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indol-8-yl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1: LiAlH4, AlCl3 / diethyl ether / 1.) 0 deg C to RT, 30 min; 2.) 2 h
2: pyridinium chlorochromate, Celite / CH2Cl2 / 3 h
3: trimethyl borate, Zn / tetrahydrofuran / 6 h
4: LiAlH4 / diethyl ether / 0.25 h
5: 80 percent / 4-dimethylaminopyridine, triethylamine / CH2Cl2 / 16 h / Ambient temperature
7: 1.) Hg(OAc)2, 90 percent HNO3; 2.) conc. HCl, Zn / 1.) Ac2O, glacial AcOH, 0 deg C, 5 min; 2.) methanol, 25 deg C, 15 min
8: CBr4, triphenylphosphine / CH2Cl2; diethyl ether / 0.5 h / 25 °C
9: 2.) 0.5 N aq. NaOH / 1.) CH2Cl2, 40 min; 2.) ether
With
hydrogenchloride; dmap; sodium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; Trimethyl borate; carbon tetrabromide; Celite; mercury(II) diacetate; nitric acid; triethylamine; triphenylphosphine; pyridinium chlorochromate; zinc;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja00299a022
- Guidance literature:
-
Multi-step reaction with 7 steps
1: trimethyl borate, Zn / tetrahydrofuran / 6 h
2: LiAlH4 / diethyl ether / 0.25 h
3: 80 percent / 4-dimethylaminopyridine, triethylamine / CH2Cl2 / 16 h / Ambient temperature
5: 1.) Hg(OAc)2, 90 percent HNO3; 2.) conc. HCl, Zn / 1.) Ac2O, glacial AcOH, 0 deg C, 5 min; 2.) methanol, 25 deg C, 15 min
6: CBr4, triphenylphosphine / CH2Cl2; diethyl ether / 0.5 h / 25 °C
7: 2.) 0.5 N aq. NaOH / 1.) CH2Cl2, 40 min; 2.) ether
With
hydrogenchloride; dmap; sodium hydroxide; lithium aluminium tetrahydride; Trimethyl borate; carbon tetrabromide; mercury(II) diacetate; nitric acid; triethylamine; triphenylphosphine; zinc;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja00299a022
- Guidance literature:
-
Multi-step reaction with 8 steps
1: pyridinium chlorochromate, Celite / CH2Cl2 / 3 h
2: trimethyl borate, Zn / tetrahydrofuran / 6 h
3: LiAlH4 / diethyl ether / 0.25 h
4: 80 percent / 4-dimethylaminopyridine, triethylamine / CH2Cl2 / 16 h / Ambient temperature
6: 1.) Hg(OAc)2, 90 percent HNO3; 2.) conc. HCl, Zn / 1.) Ac2O, glacial AcOH, 0 deg C, 5 min; 2.) methanol, 25 deg C, 15 min
7: CBr4, triphenylphosphine / CH2Cl2; diethyl ether / 0.5 h / 25 °C
8: 2.) 0.5 N aq. NaOH / 1.) CH2Cl2, 40 min; 2.) ether
With
hydrogenchloride; dmap; sodium hydroxide; lithium aluminium tetrahydride; Trimethyl borate; carbon tetrabromide; Celite; mercury(II) diacetate; nitric acid; triethylamine; triphenylphosphine; pyridinium chlorochromate; zinc;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja00299a022
