(1R,5S,8R)-tert-butyl 8-(2-chlorophenyl)-7-hydroxy-2-(4-methylphenylsulfonyl)-2-azabicyclo[3.3.1]non-6-ene-6-carboxylate

Base Information

• Chemical Name: (1R,5S,8R)-tert-butyl 8-(2-chlorophenyl)-7-hydroxy-2-(4-methylphenylsulfonyl)-2-azabicyclo[3.3.1]non-6-ene-6-carboxylate
• CAS No.: 1431726-61-2
• Molecular Formula: C₂₆H₃₀ClNO₅S
• Molecular Weight: 504.047
• Mol file: 1431726-61-2.mol

Synonyms:

Chemical Property of (1R,5S,8R)-tert-butyl 8-(2-chlorophenyl)-7-hydroxy-2-(4-methylphenylsulfonyl)-2-azabicyclo[3.3.1]non-6-ene-6-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S,8R)-tert-butyl 8-(2-chlorophenyl)-7-hydroxy-2-(4-methylphenylsulfonyl)-2-azabicyclo[3.3.1]non-6-ene-6-carboxylate

There total 7 articles about (1R,5S,8R)-tert-butyl 8-(2-chlorophenyl)-7-hydroxy-2-(4-methylphenylsulfonyl)-2-azabicyclo[3.3.1]non-6-ene-6-carboxylate 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:

N-tosyl-3-butenylamine (10285-80-0) → (1R,5S,8R)-tert-butyl 8-(2-chlorophenyl)-7-hydroxy-2-(4-methylphenylsulfonyl)-2-azabicyclo[3.3.1]non-6-ene-6-carboxylate (1431726-61-2) + (1S,5R,8S)-tert-butyl 8-(2-chlorophenyl)-7-hydroxy-2-(4-methylphenylsulfonyl)-2-azabicyclo[3.3.1]non-6-ene-6-carboxylate

Guidance literature:

Multi-step reaction with 3 steps

1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 16 h / Inert atmosphere; Reflux

2: C₃₅H₃₃NOSi; water; lithium acetate / neat (no solvent) / 24 h / 20 °C

3: lithium hydroxide monohydrate; water / isopropyl alcohol / 24 h / Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; lithium hydroxide monohydrate; C₃₅H₃₃NOSi; lithium acetate; water; In dichloromethane; isopropyl alcohol;

DOI:10.1021/ol400926p

Reference yield:

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide (18303-04-3) → (1R,5S,8R)-tert-butyl 8-(2-chlorophenyl)-7-hydroxy-2-(4-methylphenylsulfonyl)-2-azabicyclo[3.3.1]non-6-ene-6-carboxylate (1431726-61-2) + (1S,5R,8S)-tert-butyl 8-(2-chlorophenyl)-7-hydroxy-2-(4-methylphenylsulfonyl)-2-azabicyclo[3.3.1]non-6-ene-6-carboxylate

Guidance literature:

Multi-step reaction with 5 steps

1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 3 h / Inert atmosphere

2: trifluoroacetic acid / dichloromethane / 1 h / Inert atmosphere

3: Hoveyda-Grubbs catalyst second generation / dichloromethane / 16 h / Inert atmosphere; Reflux

4: C₃₅H₃₃NOSi; water; lithium acetate / neat (no solvent) / 24 h / 20 °C

5: lithium hydroxide monohydrate; water / isopropyl alcohol / 24 h / Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; lithium hydroxide monohydrate; C₃₅H₃₃NOSi; lithium acetate; water; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; isopropyl alcohol; 1: |Mitsunobu Displacement;

DOI:10.1021/ol400926p

Reference yield:

N-(but-3-en-1-yl)-N-(tert-butoxycarbonyl)-4-methylbenzenesulfonamide (208335-94-8) → (1R,5S,8R)-tert-butyl 8-(2-chlorophenyl)-7-hydroxy-2-(4-methylphenylsulfonyl)-2-azabicyclo[3.3.1]non-6-ene-6-carboxylate (1431726-61-2) + (1S,5R,8S)-tert-butyl 8-(2-chlorophenyl)-7-hydroxy-2-(4-methylphenylsulfonyl)-2-azabicyclo[3.3.1]non-6-ene-6-carboxylate

Guidance literature:

Multi-step reaction with 4 steps

1: trifluoroacetic acid / dichloromethane / 1 h / Inert atmosphere

2: Hoveyda-Grubbs catalyst second generation / dichloromethane / 16 h / Inert atmosphere; Reflux

3: C₃₅H₃₃NOSi; water; lithium acetate / neat (no solvent) / 24 h / 20 °C

4: lithium hydroxide monohydrate; water / isopropyl alcohol / 24 h / Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; lithium hydroxide monohydrate; C₃₅H₃₃NOSi; lithium acetate; water; trifluoroacetic acid; In dichloromethane; isopropyl alcohol;

DOI:10.1021/ol400926p

upstream raw materials:

tert-butyl 4-(2-chlorophenyl)-3-oxobutanoate

(E)-5-N-(4-methylphenylsulfonyl)aminopent-3-enal

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide

C₁₀H₉ClO₃