((1S,3S,4R)-2-Benzyl-2-aza-bicyclo[2.2.1]hept-5-en-3-yl)-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

Base Information

• Chemical Name: ((1S,3S,4R)-2-Benzyl-2-aza-bicyclo[2.2.1]hept-5-en-3-yl)-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone
• CAS No.: 379685-58-2
• Molecular Formula: C₂₄H₃₀N₂O₃S
• Molecular Weight: 426.58

Synonyms:((1S,3S,4R)-2-Benzyl-2-aza-bicyclo[2.2.1]hept-5-en-3-yl)-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

Chemical Property of ((1S,3S,4R)-2-Benzyl-2-aza-bicyclo[2.2.1]hept-5-en-3-yl)-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

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Technology Process of ((1S,3S,4R)-2-Benzyl-2-aza-bicyclo[2.2.1]hept-5-en-3-yl)-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

There total 3 articles about ((1S,3S,4R)-2-Benzyl-2-aza-bicyclo[2.2.1]hept-5-en-3-yl)-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone 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:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + 2-[(E)-Benzylimino]-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-ethanone (471242-92-9) → ((1S,3S,4R)-2-Benzyl-2-aza-bicyclo[2.2.1]hept-5-en-3-yl)-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (379685-58-2) + ((1R,3R,4S)-2-Benzyl-2-aza-bicyclo[2.2.1]hept-5-en-3-yl)-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone

Guidance literature:

With boron trifluoride diethyl etherate; trifluoroacetic acid; In dichloromethane; at -78 ℃; for 5h;

DOI:10.1016/S0957-4166(01)00356-1

Reference yield:

(2R)-N-glyoxylbornane-10,2-sultam (123191-45-7) → ((1S,3S,4R)-2-Benzyl-2-aza-bicyclo[2.2.1]hept-5-en-3-yl)-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (379685-58-2)

Guidance literature:

Multi-step reaction with 2 steps

1: molecular sieves 3A / CH₂Cl₂ / 0.5 h / 0 - 20 °C

2: trifluoroacetic acid; BF₃*Et₂O / CH₂Cl₂ / 5 h / -78 °C

With 3 A molecular sieve; boron trifluoride diethyl etherate; trifluoroacetic acid; In dichloromethane; 2: aza-Diels-Alder reaction;

DOI:10.1016/S0957-4166(01)00356-1

Reference yield:

benzylamine (100-46-9) → ((1S,3S,4R)-2-Benzyl-2-aza-bicyclo[2.2.1]hept-5-en-3-yl)-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (379685-58-2)

Guidance literature:

Multi-step reaction with 2 steps

1: molecular sieves 3A / CH₂Cl₂ / 0.5 h / 0 - 20 °C

2: trifluoroacetic acid; BF₃*Et₂O / CH₂Cl₂ / 5 h / -78 °C

With 3 A molecular sieve; boron trifluoride diethyl etherate; trifluoroacetic acid; In dichloromethane; 2: aza-Diels-Alder reaction;

DOI:10.1016/S0957-4166(01)00356-1

upstream raw materials:

cyclopenta-1,3-diene

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

(2R)-N-glyoxylbornane-10,2-sultam

benzylamine

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