3-(Benzyloxy)-17-(cyclopropylmethyl)-7,8-didehydro-4,5α-epoxy-14β-methoxymorphinan-6-one

Base Information

• Chemical Name: 3-(Benzyloxy)-17-(cyclopropylmethyl)-7,8-didehydro-4,5α-epoxy-14β-methoxymorphinan-6-one
• CAS No.: 131575-18-3
• Molecular Formula: C₂₈H₂₉NO₄
• Molecular Weight: 443.543
• Mol file: 131575-18-3.mol

Synonyms:3-(Benzyloxy)-17-(cyclopropylmethyl)-7,8-didehydro-4,5α-epoxy-14β-methoxymorphinan-6-one

Chemical Property of 3-(Benzyloxy)-17-(cyclopropylmethyl)-7,8-didehydro-4,5α-epoxy-14β-methoxymorphinan-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(Benzyloxy)-17-(cyclopropylmethyl)-7,8-didehydro-4,5α-epoxy-14β-methoxymorphinan-6-one

There total 5 articles about 3-(Benzyloxy)-17-(cyclopropylmethyl)-7,8-didehydro-4,5α-epoxy-14β-methoxymorphinan-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: 72.0%

3-(Benzyloxy)-7,8-didehydro-4,5α-epoxy-14β-methoxymorphinan-6-one (131575-17-2) + chloro(cyclopropyl)methane (5911-08-0) → 3-(Benzyloxy)-17-(cyclopropylmethyl)-7,8-didehydro-4,5α-epoxy-14β-methoxymorphinan-6-one (131575-18-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 90 ℃; for 20h;

DOI:10.1002/hlca.19900730622

Reference yield:

14-O-methylcodeinone (38252-24-3) → 3-(Benzyloxy)-17-(cyclopropylmethyl)-7,8-didehydro-4,5α-epoxy-14β-methoxymorphinan-6-one (131575-18-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / 48percent HBr / 0.28 h / Heating

2: 60 percent / K₂CO₃ / dimethylformamide / 20 h / Ambient temperature

3: NaHCO₃ / 1,2-dichloro-ethane / 20 h / 60 - 65 °C

4: methanol / 1 h / Heating

5: 72 percent / K₂CO₃ / dimethylformamide / 20 h / 90 °C

With hydrogen bromide; sodium hydrogencarbonate; potassium carbonate; In methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19900730622

Reference yield:

(-)-7,8-didehydro-4,5α-epoxy-3-hydroxy-14-methoxy-N-methylmorphinan-6-one hydrobromide (124942-33-2) → 3-(Benzyloxy)-17-(cyclopropylmethyl)-7,8-didehydro-4,5α-epoxy-14β-methoxymorphinan-6-one (131575-18-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / K₂CO₃ / dimethylformamide / 20 h / Ambient temperature

2: NaHCO₃ / 1,2-dichloro-ethane / 20 h / 60 - 65 °C

3: methanol / 1 h / Heating

4: 72 percent / K₂CO₃ / dimethylformamide / 20 h / 90 °C

With sodium hydrogencarbonate; potassium carbonate; In methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19900730622

upstream raw materials:

3-(Benzyloxy)-7,8-didehydro-4,5α-epoxy-14β-methoxymorphinan-6-one

chloro(cyclopropyl)methane

14-O-methylcodeinone

(-)-7,8-didehydro-4,5α-epoxy-3-hydroxy-14-methoxy-N-methylmorphinan-6-one hydrobromide