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

Base Information

• Chemical Name: 4,5α-epoxy-17-methyl-7β-(4-phenylbutyl)-6α,7α-(oxymethylene)morphinan-3-ol
• CAS No.: 85455-08-9
• Molecular Formula: C₂₈H₃₃NO₃
• Molecular Weight: 431.575
• Mol file: 85455-08-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 4,5α-epoxy-17-methyl-7β-(4-phenylbutyl)-6α,7α-(oxymethylene)morphinan-3-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:

C28H34BrNO3 (85455-25-0) → 4,5α-epoxy-17-methyl-7β-(4-phenylbutyl)-6α,7α-(oxymethylene)morphinan-3-ol (85455-08-9)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 65 - 70 ℃; for 2h; Yield given;

DOI:10.1021/jo00159a005

Reference yield:

7,7-bis<(tosyloxy)methyl>-4,5α-epoxy-3-methoxy-17-methylmorphinan-6-one (85455-00-1) → 4,5α-epoxy-17-methyl-7β-(4-phenylbutyl)-6α,7α-(oxymethylene)morphinan-3-ol (85455-08-9)

Guidance literature:

Multi-step reaction with 9 steps

1: NaBH₄ / ethanol; CHCl₃ / 1.5 h

2: 93 percent / NaOH (1N) / dioxane / 1 h / 65 - 70 °C

3: 93 percent / dimethylformamide / 18 h / 80 °C

4: 77 percent / NaOH (1N) / methanol / 1 h

5: 89 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: 82 percent / H₂ / Pd/C / ethanol / 50 °C / 2585.7 Torr / 1.) 24 h, 2.) fresh cat., H₂O, 3 d

8: 2.07 g / HBr(48percent) / 0.25 h / Heating

9: NaOH / dioxane / 2 h / 65 - 70 °C

With sodium hydroxide; sodium tetrahydroborate; TEA; hydrogen bromide; hydrogen; sodium hydride; trifluoroacetic anhydride; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jo00159a005

Reference yield:

7,7-bis(hydroxymethyl)-4,5α-epoxy-3-methoxy-17-methylmorphinan-6β-ol hydrochloride (77794-06-0) → 4,5α-epoxy-17-methyl-7β-(4-phenylbutyl)-6α,7α-(oxymethylene)morphinan-3-ol (85455-08-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 13 percent / pyridine / Ambient temperature

2: 81 percent / 1.) TFAA*Me₂SO, 2.) TEA / CH₂Cl₂ / 1.5 h / -60 °C

3: NaBH₄ / ethanol; CHCl₃ / 1.5 h

4: 93 percent / NaOH (1N) / dioxane / 1 h / 65 - 70 °C

5: 93 percent / dimethylformamide / 18 h / 80 °C

6: 77 percent / NaOH (1N) / methanol / 1 h

7: 89 percent / 1.) TFAA*Me₂SO, 2.) TEA / CH₂Cl₂ / 1.5 h / -60 °C

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

9: 82 percent / H₂ / Pd/C / ethanol / 50 °C / 2585.7 Torr / 1.) 24 h, 2.) fresh cat., H₂O, 3 d

10: 2.07 g / HBr(48percent) / 0.25 h / Heating

11: NaOH / dioxane / 2 h / 65 - 70 °C

With sodium hydroxide; sodium tetrahydroborate; TEA; hydrogen bromide; hydrogen; sodium hydride; trifluoroacetic anhydride; palladium on activated charcoal; In 1,4-dioxane; pyridine; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jo00159a005

upstream raw materials:

C₂₈H₃₄BrNO₃

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

7,7-bis<(tosyloxy)methyl>-4,5α-epoxy-3-methoxy-17-methylmorphinan-6-one

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