(4bS,8aS,9S)-benzyl 3-(benzyloxy)-1-bromo-2-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate

Base Information

Chemical Name:(4bS,8aS,9S)-benzyl 3-(benzyloxy)-1-bromo-2-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate
CAS No.:1346516-45-7
Molecular Formula:C₃₁H₃₂BrNO₄
Molecular Weight:562.503
Hs Code.:

Synonyms:(4bS,8aS,9S)-benzyl 3-(benzyloxy)-1-bromo-2-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate

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Chemical Property of (4bS,8aS,9S)-benzyl 3-(benzyloxy)-1-bromo-2-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate

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Technology Process of (4bS,8aS,9S)-benzyl 3-(benzyloxy)-1-bromo-2-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate

There total 6 articles about (4bS,8aS,9S)-benzyl 3-(benzyloxy)-1-bromo-2-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-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: 98.0%

: 1346516-44-6
(4bS,8aS,9S)-benzyl 3-(benzyloxy)-2-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate

: 1346516-45-7
(4bS,8aS,9S)-benzyl 3-(benzyloxy)-1-bromo-2-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate

Guidance literature:: With bromine; sodium acetate; In acetic acid; at 20 ℃; Inert atmosphere;

Reference yield:

: 1262869-95-3
(4bS,8aS,9S)-benzyl 2-formyl-3-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate

: 1346516-45-7
(4bS,8aS,9S)-benzyl 3-(benzyloxy)-1-bromo-2-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

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

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

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

With sulfuric acid; dihydrogen peroxide; bromine; sodium acetate; caesium carbonate; In methanol; acetic acid; N,N-dimethyl-formamide;

Reference yield:

: (+)-3-hydroxymorphinan hydrobromide

: 1346516-45-7
(4bS,8aS,9S)-benzyl 3-(benzyloxy)-1-bromo-2-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate

Guidance literature:: Multi-step reaction with 5 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

With sulfuric acid; dihydrogen peroxide; bromine; sodium acetate; caesium carbonate; triethylamine; sodium hydroxide; magnesium chloride; In 1,4-dioxane; methanol; propyl cyanide; water; acetic acid; N,N-dimethyl-formamide;