(3β)-9,10-Didehydro-2,3-dihydro-1-<(4-methoxyphenyl)sulfonyl>-6-methyl-8-methyleneergoline

Base Information

• Chemical Name: (3β)-9,10-Didehydro-2,3-dihydro-1-<(4-methoxyphenyl)sulfonyl>-6-methyl-8-methyleneergoline
• CAS No.: 89651-12-7
• Molecular Formula: C₂₃H₂₄N₂O₃S
• Molecular Weight: 408.521
• Mol file: 89651-12-7.mol

Synonyms:(3β)-9,10-Didehydro-2,3-dihydro-1-<(4-methoxyphenyl)sulfonyl>-6-methyl-8-methyleneergoline

Chemical Property of (3β)-9,10-Didehydro-2,3-dihydro-1-<(4-methoxyphenyl)sulfonyl>-6-methyl-8-methyleneergoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3β)-9,10-Didehydro-2,3-dihydro-1-<(4-methoxyphenyl)sulfonyl>-6-methyl-8-methyleneergoline

There total 14 articles about (3β)-9,10-Didehydro-2,3-dihydro-1-<(4-methoxyphenyl)sulfonyl>-6-methyl-8-methyleneergoline 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: 52.0%

(3β,8α,9α)-2,3-Dihydro-9-methanesulfonyloxy-8-methanesulfonyloxymethyl-1-<(4-methoxyphenyl)sulfonyl>-6-methylergoline (134745-89-4,134780-43-1) → (3β)-9,10-Didehydro-2,3-dihydro-1-<(4-methoxyphenyl)sulfonyl>-6-methyl-8-methyleneergoline (89651-12-7)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; for 2h; Ambient temperature;

DOI:10.1248/cpb.39.23

Reference yield: 51.0%

(3α,8α,9α,10α)-2,3-Dihydro-9-methanesulfonyloxy-8-methanesulfonyloxymethyl-1-<(4-methoxyphenyl)sulfonyl>-6-methylergoline (134745-89-4,134780-43-1) → (3β)-9,10-Didehydro-2,3-dihydro-1-<(4-methoxyphenyl)sulfonyl>-6-methyl-8-methyleneergoline (89651-12-7)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; Ambient temperature;

DOI:10.1248/cpb.39.23

Reference yield:

N-<1-<(4-Methoxyphenyl)sulfonyl>-1,2,2a,3-tetrahydrobenzindol-4-yl>-N-methyl-3-furancarboxamide (89651-06-9) → (3β)-9,10-Didehydro-2,3-dihydro-1-<(4-methoxyphenyl)sulfonyl>-6-methyl-8-methyleneergoline (89651-12-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / sodium borohydride / benzene; methanol / 4 - 5 °C / Irradiation

2: 26 percent / 1.) O₃, 2.) lithium aluminum hydride / 1.) dichloromethane, -60 deg C

3: pyridine / Ambient temperature

4: potassium t-butoxide / dimethylsulfoxide

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; potassium tert-butylate; ozone; In methanol; dimethyl sulfoxide; benzene;

upstream raw materials:

(3β,8α,9α)-2,3-Dihydro-9-methanesulfonyloxy-8-methanesulfonyloxymethyl-1-<(4-methoxyphenyl)sulfonyl>-6-methylergoline

(3α,8α,9α,10α)-2,3-Dihydro-9-methanesulfonyloxy-8-methanesulfonyloxymethyl-1-<(4-methoxyphenyl)sulfonyl>-6-methylergoline

(3α,8α,9α,10α)-2,3-Dihydro-8-hydroxymethyl-1-<(4-methoxyphenyl)sulfonyl>-6-methylergolin-9-ol

methanesulfonyl chloride

Downstream raw materials:

(+/-)-Agroclavine

(+/-)-Agroclavine I

Refernces

• 1、 Kiguchi, Toshiko,Hashimoto, Chiyomi,Ninomiya, Ichiya. "A TOTAL SYNTHESIS OF (+/-)-LYSERGENE AND (+/-)-AGROCLAVINE". . p. 43 - 47. Retrieved 2007/10/02.