N-[2-(5-methoxy-3-oxo-3,8-dihydro-3aH-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-N-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-[2-(5-methoxy-3-oxo-3,8-dihydro-3aH-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-N-methyl-benzenesulfonamide
• CAS No.: 213614-10-9
• Molecular Formula: C₂₄H₂₃NO₅S
• Molecular Weight: 437.516
• Mol file: 213614-10-9.mol

Synonyms:N-[2-(5-methoxy-3-oxo-3,8-dihydro-3aH-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-N-methyl-benzenesulfonamide

Chemical Property of N-[2-(5-methoxy-3-oxo-3,8-dihydro-3aH-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-N-methyl-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[2-(5-methoxy-3-oxo-3,8-dihydro-3aH-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-N-methyl-benzenesulfonamide

There total 1 articles about N-[2-(5-methoxy-3-oxo-3,8-dihydro-3aH-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-N-methyl-benzenesulfonamide 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: 91.0%

thebaine (115-37-7) + benzenesulfonyl bromide (2297-65-6) → N-[2-(5-methoxy-3-oxo-3,8-dihydro-3aH-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-N-methyl-benzenesulfonamide (213614-10-9)

Guidance literature:

With potassium carbonate; In water;

DOI:10.1021/jo9805394

Reference yield: 97.0%

N-[2-(5-methoxy-3-oxo-3,8-dihydro-3aH-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-N-methyl-benzenesulfonamide (213614-10-9) → N-[2-((3aR,9aR,9bS)-5-Methoxy-3-oxo-1,3,3a,8,9,9a-hexahydro-2H-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-N-methyl-benzenesulfonamide (191417-77-3)

Guidance literature:

With hydrogen; Lindlar's catalyst;

DOI:10.1021/jo9805394

Reference yield:

N-[2-(5-methoxy-3-oxo-3,8-dihydro-3aH-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-N-methyl-benzenesulfonamide (213614-10-9) → Hydrocodone (125-29-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / H₂ / Pd-CaCO₃

2: 91 percent / (TMS)Cl / CH₂Cl₂

3: 85 percent / NBS; benzoyl peroxide; Et₃N / CCl₄ / 0.67 h / Heating

4: 79 percent / tert-butanol; lithium / liquid ammonia; tetrahydrofuran / 0.5 h / -78 °C

5: 95 percent / aq. HCl / 1 h / 90 °C

With hydrogenchloride; N-Bromosuccinimide; chloro-trimethyl-silane; hydrogen; lithium; triethylamine; tert-butyl alcohol; dibenzoyl peroxide; Lindlar's catalyst; In tetrahydrofuran; tetrachloromethane; dichloromethane; ammonia; 1: Catalytic hydrogenation / 2: Cyclization / 3: Dehydrogenation / 4: Cyclization / 5: Hydrolysis;

DOI:10.1021/jo9805394

upstream raw materials:

thebaine

benzenesulfonyl bromide

Downstream raw materials:

N-[2-((3aR,9aR,9bS)-5-Methoxy-3-oxo-1,3,3a,8,9,9a-hexahydro-2H-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-N-methyl-benzenesulfonamide

1,2,3,3a(R),9a(R),9b(S)-hexahydro-5-methoxy-9b-[2-[N-methyl-N-(phenylsulfonyl)amino]ethyl]-3-(ethylenedioxy)phenanthro[4,4a,4b,5-bcd]furan

1,2,3,3a(R),8,9,9a(R),9b(S)-octahydro-5-methoxy-9b-[2-[N-methyl-N-(phenylsulfonyl)amino]ethyl]-3-(ethylenedioxy)phenanthro[4,4a,4b,5-bcd]furan

Hydrocodone