17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-1'-(5''-cyanopentyl)indolo[6,7:2',3']morphinan

Base Information

• Chemical Name: 17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-1'-(5''-cyanopentyl)indolo[6,7:2',3']morphinan
• CAS No.: 938188-27-3
• Molecular Formula: C₃₉H₄₁N₃O₅S
• Molecular Weight: 663.838
• Mol file: 938188-27-3.mol

Synonyms:17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-1'-(5''-cyanopentyl)indolo[6,7:2',3']morphinan

Chemical Property of 17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-1'-(5''-cyanopentyl)indolo[6,7:2',3']morphinan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-1'-(5''-cyanopentyl)indolo[6,7:2',3']morphinan

There total 1 articles about 17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-1'-(5''-cyanopentyl)indolo[6,7:2',3']morphinan 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: 96.0%

6-bromo-1-hexanenitrile (6621-59-6) + 17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-6,7-2',3'-indolomorphinan (221103-41-9) → 17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-1'-(5''-cyanopentyl)indolo[6,7:2',3']morphinan (938188-27-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1021/jm0700013

Reference yield: 40.0%

17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-1'-(5''-cyanopentyl)indolo[6,7:2',3']morphinan (938188-27-3) → 17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-1'-(5''-formylpentyl)indolo[6,7:2',3']morphinan (938188-28-4)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at 20 ℃; for 0.25h;

DOI:10.1021/jm0700013

Reference yield:

17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-1'-(5''-cyanopentyl)indolo[6,7:2',3']morphinan (938188-27-3) → 17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-1'-(10'''-[6''-hexyl]-[1''',4''',7''',10'''-tetraazacyclododecane-1''',4''',7'''-triacetic acid])indolo[6,7:2',3']morphinan

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / DIBAL-H / toluene; CH₂Cl₂ / 0.25 h / 20 °C

2: Et₃N; NaBH(OAc)3 / dimethylformamide / 1 h / 20 °C

With sodium tris(acetoxy)borohydride; diisobutylaluminium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm0700013

upstream raw materials:

6-bromo-1-hexanenitrile

17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-6,7-2',3'-indolomorphinan

Downstream raw materials:

17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-1'-(5''-formylpentyl)indolo[6,7:2',3']morphinan