4-methoxy-17-methyl-18-[(E)-α-methylbenzylidene]-3-(triphenylmethoxy)-5,14-ethanomorphinan-6-one

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Chemical Name:4-methoxy-17-methyl-18-[(E)-α-methylbenzylidene]-3-(triphenylmethoxy)-5,14-ethanomorphinan-6-one
CAS No.:252333-15-6
Molecular Formula:C₄₇H₄₅NO₃
Molecular Weight:671.879
Hs Code.:

Synonyms:4-methoxy-17-methyl-18-[(E)-α-methylbenzylidene]-3-(triphenylmethoxy)-5,14-ethanomorphinan-6-one

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Chemical Property of 4-methoxy-17-methyl-18-[(E)-α-methylbenzylidene]-3-(triphenylmethoxy)-5,14-ethanomorphinan-6-one

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Technology Process of 4-methoxy-17-methyl-18-[(E)-α-methylbenzylidene]-3-(triphenylmethoxy)-5,14-ethanomorphinan-6-one

There total 4 articles about 4-methoxy-17-methyl-18-[(E)-α-methylbenzylidene]-3-(triphenylmethoxy)-5,14-ethanomorphinan-6-one 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: 45.0%

: 252333-14-5
4-hydroxy-17-methyl-18-[(E)-α-methylbenzylidene]-3-(triphenylmethoxy)-5,14-ethanomorphinan-6-one

: 74-88-4
methyl iodide

: 252333-15-6
4-methoxy-17-methyl-18-[(E)-α-methylbenzylidene]-3-(triphenylmethoxy)-5,14-ethanomorphinan-6-one

Guidance literature:: 4-hydroxy-17-methyl-18-[(E)-α-methylbenzylidene]-3-(triphenylmethoxy)-5,14-ethanomorphinan-6-one; With sodium hydride; In tetrahydrofuran; at 0 ℃;

methyl iodide; With 18-crown-6 ether; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1002/(SICI)1522-2675(19991006)82:10<1721::AID-HLCA1721>3.0.CO;2-F

Reference yield:

: 16196-72-8
6,7,8,14-tetrahydro-7α-(α-hydroxy-α-methylbenzyl)-6,14-endo-ethanothebaine

: 252333-15-6
4-methoxy-17-methyl-18-[(E)-α-methylbenzylidene]-3-(triphenylmethoxy)-5,14-ethanomorphinan-6-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 80 percent / sodium propane-1-thiolate; hexamethylphosphoric triamide / 3 h / 120 °C

2.1: 56 percent / conc. HCl / 2 h / Heating

3.1: 77 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h

4.1: NaH / tetrahydrofuran / 0 °C

4.2: 45 percent / 18-crown-6 / tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydride; triethylamine; sodium 1-propanethiolate; In tetrahydrofuran; dichloromethane; 1.1: Elimination / 2.1: Rearrangement / 3.1: Etherification / 4.1: Deprotonation / 4.2: Methylation;
DOI:10.1002/(SICI)1522-2675(19991006)82:10<1721::AID-HLCA1721>3.0.CO;2-F

Reference yield:

: 188341-29-9
6,7,8,14-tetrahydro-7α-(α-hydroxy-α-methylbenzyl)-6,14-endo-ethanooripavine

: 252333-15-6
4-methoxy-17-methyl-18-[(E)-α-methylbenzylidene]-3-(triphenylmethoxy)-5,14-ethanomorphinan-6-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 56 percent / conc. HCl / 2 h / Heating

2.1: 77 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h

3.1: NaH / tetrahydrofuran / 0 °C

3.2: 45 percent / 18-crown-6 / tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; dmap; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Rearrangement / 2.1: Etherification / 3.1: Deprotonation / 3.2: Methylation;
DOI:10.1002/(SICI)1522-2675(19991006)82:10<1721::AID-HLCA1721>3.0.CO;2-F