(6S,6aS,10aS)-benzyl 12-(benzyloxy)-3,5,6,6a,7,8,9,10-octahydro-2H-6,10a-(epiminoethano)phenanthro[1,2-b][1,4]dioxine-15-carboxylate

Base Information

• Chemical Name: (6S,6aS,10aS)-benzyl 12-(benzyloxy)-3,5,6,6a,7,8,9,10-octahydro-2H-6,10a-(epiminoethano)phenanthro[1,2-b][1,4]dioxine-15-carboxylate
• CAS No.: 1346516-53-7
• Molecular Formula: C₃₃H₃₅NO₅
• Molecular Weight: 525.645
• Mol file: 1346516-53-7.mol

Synonyms:(6S,6aS,10aS)-benzyl 12-(benzyloxy)-3,5,6,6a,7,8,9,10-octahydro-2H-6,10a-(epiminoethano)phenanthro[1,2-b][1,4]dioxine-15-carboxylate

Chemical Property of (6S,6aS,10aS)-benzyl 12-(benzyloxy)-3,5,6,6a,7,8,9,10-octahydro-2H-6,10a-(epiminoethano)phenanthro[1,2-b][1,4]dioxine-15-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,6aS,10aS)-benzyl 12-(benzyloxy)-3,5,6,6a,7,8,9,10-octahydro-2H-6,10a-(epiminoethano)phenanthro[1,2-b][1,4]dioxine-15-carboxylate

There total 9 articles about (6S,6aS,10aS)-benzyl 12-(benzyloxy)-3,5,6,6a,7,8,9,10-octahydro-2H-6,10a-(epiminoethano)phenanthro[1,2-b][1,4]dioxine-15-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

(4bS,8aS,9S)-benzyl 3-(benzyloxy)-1-bromo-2-(2-hydroxyethoxy)-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate (1346516-52-6) → (6S,6aS,10aS)-benzyl 12-(benzyloxy)-3,5,6,6a,7,8,9,10-octahydro-2H-6,10a-(epiminoethano)phenanthro[1,2-b][1,4]dioxine-15-carboxylate (1346516-53-7)

Guidance literature:

With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine; In toluene; at 100 ℃; for 48h; Inert atmosphere;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (6S,6aS,10aS)-benzyl 12-(benzyloxy)-3,5,6,6a,7,8,9,10-octahydro-2H-6,10a-(epiminoethano)phenanthro[1,2-b][1,4]dioxine-15-carboxylate (1346516-53-7)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium hydroxide / 1,4-dioxane; water / 20 °C / Inert atmosphere

2: triethylamine; magnesium chloride / propyl cyanide / 192 h / 120 °C / Inert atmosphere

3: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

4: sulfuric acid; dihydrogen peroxide / methanol / 20 °C / Inert atmosphere

5: sodium acetate; bromine / acetic acid / 20 °C / Inert atmosphere

6: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

7: lithium borohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

8: sodium t-butanolate / 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 48 h / 100 °C / Inert atmosphere

With lithium borohydride; sulfuric acid; dihydrogen peroxide; bromine; sodium acetate; caesium carbonate; triethylamine; sodium hydroxide; magnesium chloride; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine; In tetrahydrofuran; 1,4-dioxane; methanol; propyl cyanide; water; acetic acid; N,N-dimethyl-formamide; toluene;

Reference yield:

N-17-Cbz-3-hydroxymorphinan (159723-96-3) → (6S,6aS,10aS)-benzyl 12-(benzyloxy)-3,5,6,6a,7,8,9,10-octahydro-2H-6,10a-(epiminoethano)phenanthro[1,2-b][1,4]dioxine-15-carboxylate (1346516-53-7)

Guidance literature:

Multi-step reaction with 7 steps

1: triethylamine; magnesium chloride / propyl cyanide / 192 h / 120 °C / Inert atmosphere

2: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3: sulfuric acid; dihydrogen peroxide / methanol / 20 °C / Inert atmosphere

4: sodium acetate; bromine / acetic acid / 20 °C / Inert atmosphere

5: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

6: lithium borohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

7: sodium t-butanolate / 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 48 h / 100 °C / Inert atmosphere

With lithium borohydride; sulfuric acid; dihydrogen peroxide; bromine; sodium acetate; caesium carbonate; triethylamine; magnesium chloride; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine; In tetrahydrofuran; methanol; propyl cyanide; acetic acid; N,N-dimethyl-formamide; toluene;

upstream raw materials:

benzyl chloroformate

N-17-Cbz-3-hydroxymorphinan

(4bS,8aS,9S)-benzyl 2-formyl-3-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate

(4bS,8aS,9S)-benzyl 3-(benzyloxy)-2-formyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate