3-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thia-4-azatricyclo-[5.2.1.0^1,5]decane-4-carbonyl)-(1S,2R,5S,6R)-4-(p-tolyl)tricyclo-[4.2.1.0^2,5]non-3-ene

Base Information

• Chemical Name: 3-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thia-4-azatricyclo-[5.2.1.0^1,5]decane-4-carbonyl)-(1S,2R,5S,6R)-4-(p-tolyl)tricyclo-[4.2.1.0^2,5]non-3-ene
• CAS No.: 1237588-70-3
• Molecular Formula: C₂₇H₃₃NO₃S
• Molecular Weight: 451.63

Synonyms:3-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thia-4-azatricyclo-[5.2.1.0^1,5]decane-4-carbonyl)-(1S,2R,5S,6R)-4-(p-tolyl)tricyclo-[4.2.1.0^2,5]non-3-ene

Chemical Property of 3-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thia-4-azatricyclo-[5.2.1.0^1,5]decane-4-carbonyl)-(1S,2R,5S,6R)-4-(p-tolyl)tricyclo-[4.2.1.0^2,5]non-3-ene

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Technology Process of 3-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thia-4-azatricyclo-[5.2.1.0^1,5]decane-4-carbonyl)-(1S,2R,5S,6R)-4-(p-tolyl)tricyclo-[4.2.1.0^2,5]non-3-ene

There total 3 articles about 3-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thia-4-azatricyclo-[5.2.1.0^1,5]decane-4-carbonyl)-(1S,2R,5S,6R)-4-(p-tolyl)tricyclo-[4.2.1.0^2,5]non-3-ene 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: 79.0%

3-tolylacetyleneacylcamphorsultam (1237588-72-5) + norbornene (498-66-8) → 3-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thia-4-azatricyclo-[5.2.1.01,5]decane-4-carbonyl)-(1S,2R,5S,6R)-4-(p-tolyl)tricyclo-[4.2.1.02,5]non-3-ene (1237588-70-3)

Guidance literature:

With chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II); In tetrahydrofuran; at 24.84 ℃; for 17h;

DOI:10.1107/S0108270109045284

Reference yield:

4-n-methylphenylacetylene (766-97-2) → 3-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thia-4-azatricyclo-[5.2.1.01,5]decane-4-carbonyl)-(1S,2R,5S,6R)-4-(p-tolyl)tricyclo-[4.2.1.02,5]non-3-ene (1237588-70-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: pivaloyl chloride; triethylamine / tetrahydrofuran / -78 - 0 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

3.1: chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) / tetrahydrofuran / 17 h / 25 °C / Inert atmosphere; Sealed tube; Darkness

With n-butyllithium; chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II); pivaloyl chloride; triethylamine; In tetrahydrofuran;

DOI:10.1021/jo501594g

Reference yield:

3-(4-methylphenyl)prop-2-ynoic acid (2227-58-9) + (2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → 3-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thia-4-azatricyclo-[5.2.1.01,5]decane-4-carbonyl)-(1S,2R,5S,6R)-4-(p-tolyl)tricyclo-[4.2.1.02,5]non-3-ene (1237588-70-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pivaloyl chloride; triethylamine / tetrahydrofuran / -78 - 0 °C / Inert atmosphere

1.2: -78 °C / Inert atmosphere

2.1: chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) / tetrahydrofuran / 17 h / 25 °C / Inert atmosphere; Sealed tube; Darkness

With chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II); pivaloyl chloride; triethylamine; In tetrahydrofuran;

DOI:10.1021/jo501594g

upstream raw materials:

3-tolylacetyleneacylcamphorsultam

norbornene

3-(4-methylphenyl)prop-2-ynoic acid

(2R)-bornane-10,2-sultam

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