endo-tert-butyl (1R,5S)-3-[(4-fluoro-2-nifrophenyl)amino]-8-azabicyclo[3.2.1]octane-8-carboxylate

Base Information

• Chemical Name: endo-tert-butyl (1R,5S)-3-[(4-fluoro-2-nifrophenyl)amino]-8-azabicyclo[3.2.1]octane-8-carboxylate
• CAS No.: 716359-01-2
• Molecular Formula: C₁₈H₂₄FN₃O₄
• Molecular Weight: 365.405

Synonyms:endo-tert-butyl (1R,5S)-3-[(4-fluoro-2-nifrophenyl)amino]-8-azabicyclo[3.2.1]octane-8-carboxylate

Chemical Property of endo-tert-butyl (1R,5S)-3-[(4-fluoro-2-nifrophenyl)amino]-8-azabicyclo[3.2.1]octane-8-carboxylate

Chemical Property:

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Technology Process of endo-tert-butyl (1R,5S)-3-[(4-fluoro-2-nifrophenyl)amino]-8-azabicyclo[3.2.1]octane-8-carboxylate

There total 2 articles about endo-tert-butyl (1R,5S)-3-[(4-fluoro-2-nifrophenyl)amino]-8-azabicyclo[3.2.1]octane-8-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: 84.0%

tert-butyl 3-endo-amino-8-azabicyclo[3.2.1]octane-8-carboxylate (207405-68-3,174486-93-2) + 1,4-difluoro-2-nitrobenzene (364-74-9) → endo-tert-butyl (1R,5S)-3-[(4-fluoro-2-nifrophenyl)amino]-8-azabicyclo[3.2.1]octane-8-carboxylate (716359-01-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 70 ℃; for 16h;

Reference yield:

1,1-dimethylethyl endo-3-[(phenylmethyl)amino]-8-azabicyclo[3.2.1]octane-8-carboxylate (207405-67-2) → endo-tert-butyl (1R,5S)-3-[(4-fluoro-2-nifrophenyl)amino]-8-azabicyclo[3.2.1]octane-8-carboxylate (716359-01-2)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / methanol

2: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 16 h / 70 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; methanol;

DOI:10.1021/jm200279v

Reference yield: 100.0%

endo-tert-butyl (1R,5S)-3-[(4-fluoro-2-nifrophenyl)amino]-8-azabicyclo[3.2.1]octane-8-carboxylate (716359-01-2) → endo-tert-butyl (1R,5S)-3-[(2-amino-4-fluorophenyl)amino]-8-azabicyclo[3.2.1]octane-8-carboxylate (716359-02-3)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In ethanol; ethyl acetate; for 16h; under 760.051 Torr;

upstream raw materials:

tert-butyl 3-endo-amino-8-azabicyclo[3.2.1]octane-8-carboxylate

1,4-difluoro-2-nitrobenzene

1,1-dimethylethyl endo-3-[(phenylmethyl)amino]-8-azabicyclo[3.2.1]octane-8-carboxylate

Downstream raw materials:

endo-tert-butyl (1R,5S)-3-[(2-amino-4-fluorophenyl)amino]-8-azabicyclo[3.2.1]octane-8-carboxylate

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