(+/-)-(14α)-4,5-epoxy-3-methoxy-6,6-(ethylenedioxy)-10-methylene-17-benzylmorphinan

Base Information

Chemical Name:(+/-)-(14α)-4,5-epoxy-3-methoxy-6,6-(ethylenedioxy)-10-methylene-17-benzylmorphinan
CAS No.:93758-41-9
Molecular Formula:C₂₇H₂₉NO₄
Molecular Weight:431.532
Hs Code.:

Synonyms:(+/-)-(14α)-4,5-epoxy-3-methoxy-6,6-(ethylenedioxy)-10-methylene-17-benzylmorphinan

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+/-)-(14α)-4,5-epoxy-3-methoxy-6,6-(ethylenedioxy)-10-methylene-17-benzylmorphinan

Chemical Property:

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Technology Process of (+/-)-(14α)-4,5-epoxy-3-methoxy-6,6-(ethylenedioxy)-10-methylene-17-benzylmorphinan

There total 18 articles about (+/-)-(14α)-4,5-epoxy-3-methoxy-6,6-(ethylenedioxy)-10-methylene-17-benzylmorphinan 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: 99.0%

: 107-21-1
ethylene glycol

: 93758-38-4
(+/-)-(14α)-4,5-epoxy-3-methoxy-10-methylene-17-benzylmorphinan-6-one

: 93758-41-9
(+/-)-(14α)-4,5-epoxy-3-methoxy-6,6-(ethylenedioxy)-10-methylene-17-benzylmorphinan

Guidance literature:: With toluene-4-sulfonic acid; In benzene; for 5h; Heating;
DOI:10.1021/jo00202a014

Reference yield:

: 6272-38-4
O-benzylcatechol

: 93758-41-9
(+/-)-(14α)-4,5-epoxy-3-methoxy-6,6-(ethylenedioxy)-10-methylene-17-benzylmorphinan

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) NaH / 1.) THF, DMF, RT, 1.5 h, 2.) RT, 12 h

2: 81 percent / H₂ / 5percent Pd/C / ethyl acetate; acetic acid / 4 h / 760 Torr

3: 59 percent / KH / tetrahydrofuran / 1.) RT, 3 h, 2.) reflux, 19 h

4: 1.) H₂O, AcOH, 2.) pyridine / 1.) THF, 80 deg C, 15 h, 2.) CH₂Cl₂, RT, 12 h

5: 99 percent / benzene; methanol; acetic acid / 6 h / Irradiation

6: 74 percent / concd. H₂SO₄ / methanol / 1.) reflux, 6 h, 2.) RT, 12 h

7: 72 percent / K₂CO₃ / acetone / 12 h / Heating

8: 90 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.2 h / 0 °C

9: 1.) HClO₄ / 1.) methanol, 0 deg C, 30 min, 2.) 0 deg C, 2 h

10: 2.) 4 N H₂SO₄ / 1a.) ether, RT, 10 min, 1b.) reflux, 30 min, 2.) RT, 1 h

11: 57 percent / trifluoromethanesulfonic acid / 2 h / Ambient temperature

12: 99 percent / p-toluenesulfonic acid monohydrate / benzene / 5 h / Heating

With pyridine; perchloric acid; trifluorormethanesulfonic acid; sulfuric acid; water; hydrogen; potassium hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; acetic acid; ethyl acetate; acetone; benzene;
DOI:10.1021/jo00202a014

Reference yield:

: 93758-13-5
2-<(methoxymethyl)oxy>-1-(benzyloxy)benzene

: 93758-41-9
(+/-)-(14α)-4,5-epoxy-3-methoxy-6,6-(ethylenedioxy)-10-methylene-17-benzylmorphinan

Guidance literature:: Multi-step reaction with 11 steps

1: 81 percent / H₂ / 5percent Pd/C / ethyl acetate; acetic acid / 4 h / 760 Torr

2: 59 percent / KH / tetrahydrofuran / 1.) RT, 3 h, 2.) reflux, 19 h

3: 1.) H₂O, AcOH, 2.) pyridine / 1.) THF, 80 deg C, 15 h, 2.) CH₂Cl₂, RT, 12 h

4: 99 percent / benzene; methanol; acetic acid / 6 h / Irradiation

5: 74 percent / concd. H₂SO₄ / methanol / 1.) reflux, 6 h, 2.) RT, 12 h

6: 72 percent / K₂CO₃ / acetone / 12 h / Heating

7: 90 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.2 h / 0 °C

8: 1.) HClO₄ / 1.) methanol, 0 deg C, 30 min, 2.) 0 deg C, 2 h

9: 2.) 4 N H₂SO₄ / 1a.) ether, RT, 10 min, 1b.) reflux, 30 min, 2.) RT, 1 h

10: 57 percent / trifluoromethanesulfonic acid / 2 h / Ambient temperature

11: 99 percent / p-toluenesulfonic acid monohydrate / benzene / 5 h / Heating

With pyridine; perchloric acid; trifluorormethanesulfonic acid; sulfuric acid; water; hydrogen; potassium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; acetic acid; ethyl acetate; acetone; benzene;
DOI:10.1021/jo00202a014