(5aR,8aR,SS)-1H-2,3,5,5a,6,7,8,8a-octahydro-9-<(4-methylphenyl)sulfinyl>-5-oxocyclopentindolizine

Base Information

• Chemical Name: (5aR,8aR,SS)-1H-2,3,5,5a,6,7,8,8a-octahydro-9-<(4-methylphenyl)sulfinyl>-5-oxocyclopentindolizine
• CAS No.: 123749-03-1
• Molecular Formula: C₁₈H₂₁NO₂S
• Molecular Weight: 315.436

Synonyms:

Chemical Property of (5aR,8aR,SS)-1H-2,3,5,5a,6,7,8,8a-octahydro-9-<(4-methylphenyl)sulfinyl>-5-oxocyclopentindolizine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5aR,8aR,SS)-1H-2,3,5,5a,6,7,8,8a-octahydro-9-<(4-methylphenyl)sulfinyl>-5-oxocyclopentindolizine

There total 4 articles about (5aR,8aR,SS)-1H-2,3,5,5a,6,7,8,8a-octahydro-9-<(4-methylphenyl)sulfinyl>-5-oxocyclopentindolizine 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:

(R)-methyl p-tolyl sulfoxide (1519-39-7) → (5aR,8aR,SS)-1H-2,3,5,5a,6,7,8,8a-octahydro-9-<(4-methylphenyl)sulfinyl>-5-oxocyclopentindolizine (123749-03-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) ethylmagnesium bromide, diisopropylamine / 1.) THF, 0 deg C, 45 min, 2.) HMPA, 0 deg C, 30 min

2: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) a) -78 deg C, 15 min, b) 25 deg C, 2 h

With ethylmagnesium bromide; diisopropylamine; lithium diisopropyl amide;

DOI:10.1021/jo00025a011

Reference yield:

ethyl cyclopent-1-enecarboxylate (10267-94-4) + (+)-(R)-4,5-dihydro-2-<<(4-methylphenyl)sulfinyl>methyl>-3H-pyrrole (123642-79-5) → (5aS,8aR,SS)-1H-9-<(4-methylphenyl)sulfinyl>-2,3,5,5a,6,7,8,8a-octahydro-5-oxocyclopentindolizine (123642-83-1) + (5aR,8aR,SS)-1H-2,3,5,5a,6,7,8,8a-octahydro-9-<(4-methylphenyl)sulfinyl>-5-oxocyclopentindolizine (123749-03-1)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction. Yields of byproduct given; 1.) a.) THF, -78 deg C, 30 min, b.) -30 deg C, 15 min, 2.) a.) -78 deg C, 15 min, b.) 25 deg C, 4 h;

DOI:10.1021/jo00285a009

Reference yield:

2-methyl-1H-pyrroline (872-32-2) → (5aR,8aR,SS)-1H-2,3,5,5a,6,7,8,8a-octahydro-9-<(4-methylphenyl)sulfinyl>-5-oxocyclopentindolizine (123749-03-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium diisopropylamide (LDA) / 1.) THF, 0 deg C, 15 min, 2.) -50 deg C, 1 h

2: 1.) n-BuLi / 1.) a.) THF, -78 deg C, 30 min, b.) -30 deg C, 15 min, 2.) a.) -78 deg C, 15 min, b.) 25 deg C, 4 h

With n-butyllithium; lithium diisopropyl amide;

DOI:10.1021/jo00285a009

upstream raw materials:

ethyl cyclopent-1-enecarboxylate

(+)-(R)-4,5-dihydro-2-<<(4-methylphenyl)sulfinyl>methyl>-3H-pyrrole

(R)-methyl p-tolyl sulfoxide

2-methyl-1H-pyrroline

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