Technology Process of (R,S)-(1l,2u,3l,5u,7l)-2-(benzyloxy)-3-methylbicyclo<3.3.1>nonanespiro-7,2'-1'-oxacyclopropane
There total 9 articles about (R,S)-(1l,2u,3l,5u,7l)-2-(benzyloxy)-3-methylbicyclo<3.3.1>nonanespiro-7,2'-1'-oxacyclopropane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 83 percent / 1 M NaOH / dioxane / 16 h / 185 °C
2: 99 percent / H2 / 5percent Pd/C / ethanol / 0.5 h
3: 88 percent / trimethyl orthoformate, p-toluenesulfonic acid / toluene / 1.5 h / Heating
4: 1.) BH3*THF, 2.) 10percent aq. NaOH, 30percent aq. H2O2 / 1.) RT, 1 h, 2.) a) RT, 1 h, b) 40 deg C, 20 min
5: 88 percent / KH, tetrabutylammonium iodide / 1,2-dimethoxy-ethane / 1 h / 55 °C
6: 96 percent / 1 M aq. HCl / tetrahydrofuran / 3 h / Ambient temperature
7: 1.) KH / 1.) DMSO, RT, 5 min, 2.) RT, 18 h
With
hydrogenchloride; sodium hydroxide; borane-THF; hydrogen; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; potassium hydride; toluene-4-sulfonic acid; trimethyl orthoformate;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; toluene;
DOI:10.1021/ja00006a042
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 87 percent / Br2, AlBr3, BBr3 / 1.5 h / 85 °C
2: 83 percent / 1 M NaOH / dioxane / 16 h / 185 °C
3: 99 percent / H2 / 5percent Pd/C / ethanol / 0.5 h
4: 88 percent / trimethyl orthoformate, p-toluenesulfonic acid / toluene / 1.5 h / Heating
5: 1.) BH3*THF, 2.) 10percent aq. NaOH, 30percent aq. H2O2 / 1.) RT, 1 h, 2.) a) RT, 1 h, b) 40 deg C, 20 min
6: 88 percent / KH, tetrabutylammonium iodide / 1,2-dimethoxy-ethane / 1 h / 55 °C
7: 96 percent / 1 M aq. HCl / tetrahydrofuran / 3 h / Ambient temperature
8: 1.) KH / 1.) DMSO, RT, 5 min, 2.) RT, 18 h
With
hydrogenchloride; sodium hydroxide; aluminum tri-bromide; borane-THF; hydrogen; dihydrogen peroxide; bromine; boron tribromide; tetra-(n-butyl)ammonium iodide; potassium hydride; toluene-4-sulfonic acid; trimethyl orthoformate;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; toluene;
DOI:10.1021/ja00006a042
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 88 percent / Br2 / 2 h / 105 °C
2: 87 percent / Br2, AlBr3, BBr3 / 1.5 h / 85 °C
3: 83 percent / 1 M NaOH / dioxane / 16 h / 185 °C
4: 99 percent / H2 / 5percent Pd/C / ethanol / 0.5 h
5: 88 percent / trimethyl orthoformate, p-toluenesulfonic acid / toluene / 1.5 h / Heating
6: 1.) BH3*THF, 2.) 10percent aq. NaOH, 30percent aq. H2O2 / 1.) RT, 1 h, 2.) a) RT, 1 h, b) 40 deg C, 20 min
7: 88 percent / KH, tetrabutylammonium iodide / 1,2-dimethoxy-ethane / 1 h / 55 °C
8: 96 percent / 1 M aq. HCl / tetrahydrofuran / 3 h / Ambient temperature
9: 1.) KH / 1.) DMSO, RT, 5 min, 2.) RT, 18 h
With
hydrogenchloride; sodium hydroxide; aluminum tri-bromide; borane-THF; hydrogen; dihydrogen peroxide; bromine; boron tribromide; tetra-(n-butyl)ammonium iodide; potassium hydride; toluene-4-sulfonic acid; trimethyl orthoformate;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; toluene;
DOI:10.1021/ja00006a042
