7β-(chloromethyl)-4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenylbutyl)morphinan-6β-ol

Base Information

Chemical Name:7β-(chloromethyl)-4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenylbutyl)morphinan-6β-ol
CAS No.:85454-98-4
Molecular Formula:C₂₉H₃₆ClNO₃
Molecular Weight:482.063
Hs Code.:

Synonyms:7β-(chloromethyl)-4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenylbutyl)morphinan-6β-ol

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Chemical Property of 7β-(chloromethyl)-4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenylbutyl)morphinan-6β-ol

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Technology Process of 7β-(chloromethyl)-4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenylbutyl)morphinan-6β-ol

There total 9 articles about 7β-(chloromethyl)-4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenylbutyl)morphinan-6β-ol 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: 29.0%

: 85454-97-3
4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenyl-1,3-butadienyl)-6β,7β-(oxymethylene)morphinan

: 85454-98-4
7β-(chloromethyl)-4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenylbutyl)morphinan-6β-ol

: 85454-99-5
4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenylbutyl)-6β,7β-(oxymethylene)morphinan

Guidance literature:: With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; for 3h; under 2585.7 Torr;
DOI:10.1021/jo00159a005

Reference yield:

: 77794-06-0
7,7-bis(hydroxymethyl)-4,5α-epoxy-3-methoxy-17-methylmorphinan-6β-ol hydrochloride

: 85454-98-4
7β-(chloromethyl)-4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenylbutyl)morphinan-6β-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 13 percent / pyridine / Ambient temperature

2: 73 percent / 1N NaOH / butan-2-one / 2 h / Heating

3: 97 percent / dimethylformamide / 18 h / 100 °C

4: 66 percent / NaOMe / methanol / 0.5 h

5: 72 percent / 1.) TFAA*Me₂SO, 2.) TEA / CH₂Cl₂ / 1.5 h / -60 °C

6: 1.) NaH / 1.) DMSO, 25 deg C, 10 min, 2.) DMSO, room temp., 30 min, 65-70 deg C, 30 min

7: 47 percent / aq. HCl, H₂ / Pd/C / ethanol / 3 h / 2585.7 Torr

With hydrogenchloride; sodium hydroxide; TEA; hydrogen; sodium methylate; sodium hydride; trifluoroacetic anhydride; palladium on activated charcoal; In pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; butanone;
DOI:10.1021/jo00159a005

Reference yield:

: 77794-00-4
7,7-bis<(tosyloxy)methyl>-4,5α-epoxy-3-methoxy-17-methylmorphinan-6β-ol

: 85454-98-4
7β-(chloromethyl)-4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenylbutyl)morphinan-6β-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 73 percent / 1N NaOH / butan-2-one / 2 h / Heating

2: 97 percent / dimethylformamide / 18 h / 100 °C

3: 66 percent / NaOMe / methanol / 0.5 h

4: 72 percent / 1.) TFAA*Me₂SO, 2.) TEA / CH₂Cl₂ / 1.5 h / -60 °C

5: 1.) NaH / 1.) DMSO, 25 deg C, 10 min, 2.) DMSO, room temp., 30 min, 65-70 deg C, 30 min

6: 47 percent / aq. HCl, H₂ / Pd/C / ethanol / 3 h / 2585.7 Torr

With hydrogenchloride; sodium hydroxide; TEA; hydrogen; sodium methylate; sodium hydride; trifluoroacetic anhydride; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; butanone;
DOI:10.1021/jo00159a005