Technology Process of (1R,3S,5R)-tert-butyl 3-formyl-2-azabicyclo[3.1.0]hexane-2-carboxylate
There total 1 articles about (1R,3S,5R)-tert-butyl 3-formyl-2-azabicyclo[3.1.0]hexane-2-carboxylate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 8 steps
1.1: dmap; triethylamine / dichloromethane / 20 °C
2.1: dmap; triethylamine / dichloromethane / 18.16 h / 24 °C
3.1: lithium triethylborohydride / toluene; tetrahydrofuran / 1.08 h / -50 - -45 °C
3.2: 14.42 h / -50 - 20 °C
3.3: 0.08 h / Cooling with ice/water
4.1: diethylzinc / toluene / 0.25 h / -30 °C
4.2: 19.66 h / -25 - -21 °C
4.3: 0.33 h / -25 - 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4.83 h / 20 °C
6.1: sodium periodate; ruthenium trichloride / tetrachloromethane; acetonitrile; water / 1.25 h
7.1: borane-THF / tetrahydrofuran / 3.5 h / 0 °C / Reflux
7.2: 0 °C
8.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
With
dmap; ruthenium trichloride; sodium periodate; borane-THF; tetrabutyl ammonium fluoride; diethylzinc; lithium triethylborohydride; Dess-Martin periodane; triethylamine;
In
tetrahydrofuran; tetrachloromethane; dichloromethane; water; toluene; acetonitrile;
- Guidance literature:
-
Multi-step reaction with 5 steps
1: ammonia / methanol / 15.58 h / 20 °C
2: N-Bromosuccinimide / tetrahydrofuran / 4.5 h / 20 °C
3: ethylenediaminetetraacetic acid; ammonia; zinc / methanol; water / 6 h / 20 °C
4: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 6 h / 95 °C / Inert atmosphere
5: potassium carbonate; XPhos / tris(dibenzylideneacetone)dipalladium(0) chloroform complex / 1,4-dioxane / 8 h / 110 °C / Inert atmosphere
With
N-Bromosuccinimide; ethylenediaminetetraacetic acid; ammonia; sodium carbonate; potassium carbonate; zinc; XPhos;
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
In
tetrahydrofuran; 1,4-dioxane; methanol; water;
- Guidance literature:
-
Multi-step reaction with 6 steps
1: ammonia / methanol / 15.58 h / 20 °C
2: N-Bromosuccinimide / tetrahydrofuran / 4.5 h / 20 °C
3: ethylenediaminetetraacetic acid; ammonia; zinc / methanol; water / 6 h / 20 °C
4: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 6 h / 95 °C / Inert atmosphere
5: potassium carbonate; XPhos / tris(dibenzylideneacetone)dipalladium(0) chloroform complex / 1,4-dioxane / 8 h / 110 °C / Inert atmosphere
6: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 6 h / 95 °C
With
N-Bromosuccinimide; ethylenediaminetetraacetic acid; ammonia; sodium carbonate; potassium carbonate; zinc; XPhos;
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
In
tetrahydrofuran; 1,4-dioxane; methanol; water;
