Technology Process of N-benzyl-8β-(2-hydroxyethyl)-7α-<<(tert-butyldimethylsilyl)oxy>-methyl>-endo-ethylenetetrahydronorthebaine
There total 10 articles about N-benzyl-8β-(2-hydroxyethyl)-7α-<<(tert-butyldimethylsilyl)oxy>-methyl>-endo-ethylenetetrahydronorthebaine which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 84 percent / Et3N / CH2Cl2 / Ambient temperature
2: 99 percent / benzene / 7 h / Heating
3: 64 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / Heating
4: 1.) KH, 2.) n-BuLi
5: 97 percent / oxalyl chloride, DMSO / CH2Cl2 / 1 h / -78 - -40 °C
6: 52 percent / silica gel / CHCl3 / 48 h
7: 84 percent / tetrahydrofuran / 25 h / Ambient temperature
8: 89 percent / KH / tetrahydrofuran / 24 h / Ambient temperature
9: 1.) BH3*THF, 2.) aq. NaOH, H2O2 / 1.) RT, 1 h, 2.) THF, RT, 3.5 h
With
sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; borane-THF; oxalyl dichloride; dihydrogen peroxide; silica gel; potassium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; dichloromethane; chloroform; benzene;
DOI:10.1021/jm00394a016
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 84 percent / Et3N / CH2Cl2 / Ambient temperature
2: 99 percent / benzene / 7 h / Heating
3: 64 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / Heating
4: 1.) KH, 2.) n-BuLi
5: 97 percent / oxalyl chloride, DMSO / CH2Cl2 / 1 h / -78 - -40 °C
6: 52 percent / silica gel / CHCl3 / 48 h
7: 84 percent / tetrahydrofuran / 25 h / Ambient temperature
8: 89 percent / KH / tetrahydrofuran / 24 h / Ambient temperature
9: 1.) BH3*THF, 2.) aq. NaOH, H2O2 / 1.) RT, 1 h, 2.) THF, RT, 3.5 h
With
sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; borane-THF; oxalyl dichloride; dihydrogen peroxide; silica gel; potassium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; dichloromethane; chloroform; benzene;
DOI:10.1021/jm00394a016
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 99 percent / benzene / 7 h / Heating
2: 64 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / Heating
3: 1.) KH, 2.) n-BuLi
4: 97 percent / oxalyl chloride, DMSO / CH2Cl2 / 1 h / -78 - -40 °C
5: 52 percent / silica gel / CHCl3 / 48 h
6: 84 percent / tetrahydrofuran / 25 h / Ambient temperature
7: 89 percent / KH / tetrahydrofuran / 24 h / Ambient temperature
8: 1.) BH3*THF, 2.) aq. NaOH, H2O2 / 1.) RT, 1 h, 2.) THF, RT, 3.5 h
With
sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; borane-THF; oxalyl dichloride; dihydrogen peroxide; silica gel; potassium hydride; dimethyl sulfoxide;
In
tetrahydrofuran; dichloromethane; chloroform; benzene;
DOI:10.1021/jm00394a016
