(-)-(7R,SS)-1,2,3,5,6,7-hexahydro-7-methyl-8-<(4-methylphenyl)sulfinyl>-5-indolizinone

Base Information

• Chemical Name: (-)-(7R,SS)-1,2,3,5,6,7-hexahydro-7-methyl-8-<(4-methylphenyl)sulfinyl>-5-indolizinone
• CAS No.: 137119-54-1
• Molecular Formula: C₁₆H₁₉NO₂S
• Molecular Weight: 289.398
• Mol file: 137119-54-1.mol

Synonyms:(-)-(7R,SS)-1,2,3,5,6,7-hexahydro-7-methyl-8-<(4-methylphenyl)sulfinyl>-5-indolizinone

Chemical Property of (-)-(7R,SS)-1,2,3,5,6,7-hexahydro-7-methyl-8-<(4-methylphenyl)sulfinyl>-5-indolizinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(7R,SS)-1,2,3,5,6,7-hexahydro-7-methyl-8-<(4-methylphenyl)sulfinyl>-5-indolizinone

There total 5 articles about (-)-(7R,SS)-1,2,3,5,6,7-hexahydro-7-methyl-8-<(4-methylphenyl)sulfinyl>-5-indolizinone 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: 53.0%

crotonic acid methyl ester (623-43-8) + (+)-(R)-4,5-dihydro-2-<<(4-methylphenyl)sulfinyl>methyl>-3H-pyrrole (123642-79-5) → (-)-(7R,SS)-1,2,3,5,6,7-hexahydro-7-methyl-8-<(4-methylphenyl)sulfinyl>-5-indolizinone (137119-54-1,129762-22-7) + (+)-(7S,SS)-1,2,3,5,6,7-hexahydro-7-methyl-8-<(4-methylphenyl)sulfinyl>-5-indolizinone (137119-55-2,129762-22-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 25 ℃; Mechanism; other substrates;

DOI:10.1021/jo00025a011

Reference yield:

isopropyl crotonate (6284-46-4) + (+)-(R)-4,5-dihydro-2-<<(4-methylphenyl)sulfinyl>methyl>-3H-pyrrole (123642-79-5) → (+)-(6R,7R,SS)-1,2,3,5,6,7-hexahydro-6-<2-(isopropoxycarbonyl)-1-methylethyl>-7-methyl-8-<(4-methylphenyl)sulfinyl>-5-indolizinone (137008-15-2) + (-)-(7R,SS)-1,2,3,5,6,7-hexahydro-7-methyl-8-<(4-methylphenyl)sulfinyl>-5-indolizinone (137119-54-1,129762-22-7)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, -78 deg C, 1 h, 2.) a) -78 deg C, b) 25 deg C, 2 h;

DOI:10.1021/jo00025a011

Reference yield:

(R)-methyl p-tolyl sulfoxide (1519-39-7) → (-)-(7R,SS)-1,2,3,5,6,7-hexahydro-7-methyl-8-<(4-methylphenyl)sulfinyl>-5-indolizinone (137119-54-1,129762-22-7)

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, b) 25 deg C, 2 h

With ethylmagnesium bromide; diisopropylamine; lithium diisopropyl amide;

DOI:10.1021/jo00025a011

upstream raw materials:

isopropyl crotonate

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

(Z)-methyl but-2-enoate

crotonic acid methyl ester

Refernces