(S_S,7S)-3,3-pentamethylene-7-phenyl-8-(p-tolylsulfinyl)-1,2,3,5,6,7-hexahydro-2-oxa-5-indolizinone

Base Information

• Chemical Name: (S_S,7S)-3,3-pentamethylene-7-phenyl-8-(p-tolylsulfinyl)-1,2,3,5,6,7-hexahydro-2-oxa-5-indolizinone
• CAS No.: 244104-74-3
• Molecular Formula: C₂₅H₂₇NO₃S
• Molecular Weight: 421.56
• Mol file: 244104-74-3.mol

Synonyms:(S_S,7S)-3,3-pentamethylene-7-phenyl-8-(p-tolylsulfinyl)-1,2,3,5,6,7-hexahydro-2-oxa-5-indolizinone

Chemical Property of (S_S,7S)-3,3-pentamethylene-7-phenyl-8-(p-tolylsulfinyl)-1,2,3,5,6,7-hexahydro-2-oxa-5-indolizinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S_S,7S)-3,3-pentamethylene-7-phenyl-8-(p-tolylsulfinyl)-1,2,3,5,6,7-hexahydro-2-oxa-5-indolizinone

There total 4 articles about (S_S,7S)-3,3-pentamethylene-7-phenyl-8-(p-tolylsulfinyl)-1,2,3,5,6,7-hexahydro-2-oxa-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: 61.0%

Methyl cinnamate (103-26-4,1754-62-7) + (+)-(RS)-3-{[(4-methylphenyl)sulfinyl]methyl}-1-oxa-4-azaspiro[4.5]dec-3-ene (146860-26-6) → (SS,7S)-3,3-pentamethylene-7-phenyl-8-(p-tolylsulfinyl)-1,2,3,5,6,7-hexahydro-2-oxa-5-indolizinone (244104-74-3)

Guidance literature:

(+)-(R_S)-3-{[(4-methylphenyl)sulfinyl]methyl}-1-oxa-4-azaspiro[4.5]dec-3-ene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

Methyl cinnamate; In tetrahydrofuran; hexane; at 20 ℃; for 2h; Further stages.;

DOI:10.1016/j.tetasy.2008.05.030

Reference yield:

Methyl cinnamate (103-26-4,1754-62-7) + (+)-(RS)-3-{[(4-methylphenyl)sulfinyl]methyl}-1-oxa-4-azaspiro[4.5]dec-3-ene (146860-26-6) → (SS,7S)-3,3-pentamethylene-7-phenyl-8-(p-tolylsulfinyl)-1,2,3,5,6,7-hexahydro-2-oxa-5-indolizinone (244104-74-3) + (SS,7R)-3,3-pentamethylene-7-phenyl-8-(p-tolylsulfinyl)-1,2,3,5,6,7-hexahydro-2-oxa-5-indolizinone

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(99)01047-3

Reference yield:

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate (1517-82-4) → (SS,7S)-3,3-pentamethylene-7-phenyl-8-(p-tolylsulfinyl)-1,2,3,5,6,7-hexahydro-2-oxa-5-indolizinone (244104-74-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2 h / -78 °C

2: n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; 2: Michael reaction;

DOI:10.1016/S0957-4166(01)00553-5

upstream raw materials:

Methyl cinnamate

(+)-(R_S)-3-{[(4-methylphenyl)sulfinyl]methyl}-1-oxa-4-azaspiro[4.5]dec-3-ene

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

4-methyl-2,2-pentamethylene-2,5-dihydrooxazole

Downstream raw materials:

C₃₅H₃₇NO₅S