Technology Process of 5-[(4aR,6R,8aS)-2-amino-6-[(benzyloxy)methyl]-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-4-fluoro-2-methoxybenzonitrile
There total 10 articles about 5-[(4aR,6R,8aS)-2-amino-6-[(benzyloxy)methyl]-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-4-fluoro-2-methoxybenzonitrile which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
1,8-diazabicyclo[5.4.0]undec-7-ene;
for 18h;
Reflux;
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 30 °C
1.2: 19 h / 20 - 70 °C
2.1: formic acid; water / 2.5 h / 20 °C
2.2: 18 h / 20 °C
3.1: sodium hypochlorite / water; dichloromethane / 1.5 h / 0 - 15 °C
4.1: boron trifluoride diethyl etherate / toluene; isopropyl alcohol / 0.5 h / -74 °C / Inert atmosphere
4.2: 1.5 h / -78 - 5 °C
5.1: samarium iodide / tetrahydrofuran / 1.5 h / 0 - 20 °C
6.1: dichloromethane / 18 h / 20 °C
7.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 3.5 h / -50 - 0 °C
8.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 2 h / 80 °C / Microwave irradiation; Inert atmosphere; Sealed tube
9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 18 h / Reflux
With
pyridine; sodium hypochlorite; tetrakis(triphenylphosphine) palladium(0); formic acid; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; water; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; mineral oil;
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: formic acid; water / 2.5 h / 20 °C
1.2: 18 h / 20 °C
2.1: sodium hypochlorite / water; dichloromethane / 1.5 h / 0 - 15 °C
3.1: boron trifluoride diethyl etherate / toluene; isopropyl alcohol / 0.5 h / -74 °C / Inert atmosphere
3.2: 1.5 h / -78 - 5 °C
4.1: samarium iodide / tetrahydrofuran / 1.5 h / 0 - 20 °C
5.1: dichloromethane / 18 h / 20 °C
6.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 3.5 h / -50 - 0 °C
7.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 2 h / 80 °C / Microwave irradiation; Inert atmosphere; Sealed tube
8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 18 h / Reflux
With
pyridine; sodium hypochlorite; tetrakis(triphenylphosphine) palladium(0); formic acid; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; water; 1,8-diazabicyclo[5.4.0]undec-7-ene;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene;