Technology Process of cis-4aα-<2-(benzyloxy)ethyl>-1-(methoxycarbonyl)-4-(phenylthio)-1,2,3,4,5,6,7,7α-octahydro-7H-1-pyrindin-7-ol
There total 10 articles about cis-4aα-<2-(benzyloxy)ethyl>-1-(methoxycarbonyl)-4-(phenylthio)-1,2,3,4,5,6,7,7α-octahydro-7H-1-pyrindin-7-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 99 percent / 50percent aq. NaOH, (n-Bu)4NHSO4 / 0.75 h / 23 °C
2: 16.6 g / water, pyridine p-toluenesulfonate (PPTS) / acetone / 16 h / Heating
3: Et3N / dimethylformamide / 96 h / 130 °C
4: ZnBr2 / CH2Cl2 / 1 h / 23 °C
5: NaHCO3, NaI / butan-2-one / 1.) 23 deg C, 22 h, 2.) reflux, 20 h
6: liq. NH3 / CHCl3 / 72 h / 5171.5 Torr / Ambient temperature
7: KHCO3 / CHCl3 / 14 h / 23 °C
8: 1.) BH3, 2.) 3 M NaOH, 30percent aq. H2O2 / 1.) THF, 23 deg C, 45 min, 2.) 23 deg C, 2 h
With
sodium hydroxide; borane; ammonia; water; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium hydrogencarbonate; triethylamine; sodium iodide; zinc dibromide;
In
dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; butanone;
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 86 percent / pyridine p-toluenesulfonate (PPTS) / toluene / 12 h / Heating
2: 92 percent / LiAlH4 / diethyl ether / 1.) 0 deg C, 1 h, 2.) 23 deg C, 1 h
3: 99 percent / 50percent aq. NaOH, (n-Bu)4NHSO4 / 0.75 h / 23 °C
4: 16.6 g / water, pyridine p-toluenesulfonate (PPTS) / acetone / 16 h / Heating
5: Et3N / dimethylformamide / 96 h / 130 °C
6: ZnBr2 / CH2Cl2 / 1 h / 23 °C
7: NaHCO3, NaI / butan-2-one / 1.) 23 deg C, 22 h, 2.) reflux, 20 h
8: liq. NH3 / CHCl3 / 72 h / 5171.5 Torr / Ambient temperature
9: KHCO3 / CHCl3 / 14 h / 23 °C
10: 1.) BH3, 2.) 3 M NaOH, 30percent aq. H2O2 / 1.) THF, 23 deg C, 45 min, 2.) 23 deg C, 2 h
With
sodium hydroxide; lithium aluminium tetrahydride; borane; ammonia; water; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium hydrogencarbonate; triethylamine; sodium iodide; zinc dibromide;
In
diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; toluene; butanone;
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 92 percent / LiAlH4 / diethyl ether / 1.) 0 deg C, 1 h, 2.) 23 deg C, 1 h
2: 99 percent / 50percent aq. NaOH, (n-Bu)4NHSO4 / 0.75 h / 23 °C
3: 16.6 g / water, pyridine p-toluenesulfonate (PPTS) / acetone / 16 h / Heating
4: Et3N / dimethylformamide / 96 h / 130 °C
5: ZnBr2 / CH2Cl2 / 1 h / 23 °C
6: NaHCO3, NaI / butan-2-one / 1.) 23 deg C, 22 h, 2.) reflux, 20 h
7: liq. NH3 / CHCl3 / 72 h / 5171.5 Torr / Ambient temperature
8: KHCO3 / CHCl3 / 14 h / 23 °C
9: 1.) BH3, 2.) 3 M NaOH, 30percent aq. H2O2 / 1.) THF, 23 deg C, 45 min, 2.) 23 deg C, 2 h
With
sodium hydroxide; lithium aluminium tetrahydride; borane; ammonia; water; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium hydrogencarbonate; triethylamine; sodium iodide; zinc dibromide;
In
diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; butanone;
