1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-(4-isobutyl-phenyl)-ethanone

Base Information

• Chemical Name: 1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-(4-isobutyl-phenyl)-ethanone
• CAS No.: 188650-93-3
• Molecular Formula: C₂₂H₃₁NO₃S
• Molecular Weight: 389.559

Synonyms:1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-(4-isobutyl-phenyl)-ethanone

Chemical Property of 1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-(4-isobutyl-phenyl)-ethanone

Chemical Property:

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Technology Process of 1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-(4-isobutyl-phenyl)-ethanone

There total 1 articles about 1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-(4-isobutyl-phenyl)-ethanone 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%

p-isobutylphenylacetic acid methyl ester (61566-33-4) + (+)-camphorsultam (108448-77-7,124224-04-0) → 1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-(4-isobutyl-phenyl)-ethanone (188650-93-3)

Guidance literature:

With trimethylaluminum; In dichloromethane; Heating;

DOI:10.1016/S0040-4039(97)00148-2

Reference yield:

1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-(4-isobutyl-phenyl)-ethanone (188650-93-3) → (S)-ibuprofen (51146-56-6,58560-75-1)

Guidance literature:

Multi-step reaction with 2 steps

1: n-BuLi, N,N-dimethylpropyleneurea / -60 °C

2: 89 percent / LiOH, H₂O₂ / tetrahydrofuran; H₂O

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; n-butyllithium; dihydrogen peroxide; In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(97)00148-2

Reference yield:

1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-(4-isobutyl-phenyl)-ethanone (188650-93-3) + methyl iodide (74-88-4) → (R)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-(4-isobutyl-phenyl)-propan-1-one + (S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-(4-isobutyl-phenyl)-propan-1-one (188650-94-4)

Guidance literature:

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; at -60 ℃; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(97)00148-2

upstream raw materials:

p-isobutylphenylacetic acid methyl ester

(+)-camphorsultam

Downstream raw materials:

(S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-(4-isobutyl-phenyl)-propan-1-one

(S)-ibuprofen

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