3-{2-fluoro-5-[(2,2,2-trifluoro-acetylamino)-methyl]-phenyl}-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester

Base Information

Chemical Name:3-{2-fluoro-5-[(2,2,2-trifluoro-acetylamino)-methyl]-phenyl}-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester
CAS No.:1314641-63-8
Molecular Formula:C₂₁H₂₄F₄N₂O₃
Molecular Weight:428.427
Hs Code.:

Synonyms:3-{2-fluoro-5-[(2,2,2-trifluoro-acetylamino)-methyl]-phenyl}-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester

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Chemical Property of 3-{2-fluoro-5-[(2,2,2-trifluoro-acetylamino)-methyl]-phenyl}-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester

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Technology Process of 3-{2-fluoro-5-[(2,2,2-trifluoro-acetylamino)-methyl]-phenyl}-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester

There total 2 articles about 3-{2-fluoro-5-[(2,2,2-trifluoro-acetylamino)-methyl]-phenyl}-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester 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: 69.0%

: 1314641-62-7
N-(3-bromo-4-fluoro-benzyl)-2,2,2-trifluoroacetamide

: 185099-68-7,1245646-51-8
tert‐butyl 3‐(trifluoromethanesulfonyloxy)‐8‐azabicyclo[3.2.1]oct‐2‐ene‐8‐carboxylate

: 1314641-63-8
3-{2-fluoro-5-[(2,2,2-trifluoro-acetylamino)-methyl]-phenyl}-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester

Guidance literature:: tert‐butyl 3‐(trifluoromethanesulfonyloxy)‐8‐azabicyclo[3.2.1]oct‐2‐ene‐8‐carboxylate; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hexamethyldistannane; lithium chloride; In tetrahydrofuran; at 80 ℃; for 6h;

N-(3-bromo-4-fluoro-benzyl)-2,2,2-trifluoroacetamide; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 110 ℃;
DOI:10.1016/j.bmcl.2011.12.127

Reference yield:

: 202865-68-7
3-bromo-4-fluoro-benzylamine hydrochloride

: 1314641-63-8
3-{2-fluoro-5-[(2,2,2-trifluoro-acetylamino)-methyl]-phenyl}-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylamine / ethyl acetate / 0.2 h / 0 °C

1.2: 2.03 h / 0 °C

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; hexamethyldistannane; lithium chloride / tetrahydrofuran / 6 h / 80 °C

2.2: 110 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hexamethyldistannane; triethylamine; lithium chloride; In tetrahydrofuran; ethyl acetate; 2.2: Stille coupling;
DOI:10.1016/j.bmcl.2011.12.127

Reference yield: 90.0%

: 1314641-63-8
3-{2-fluoro-5-[(2,2,2-trifluoro-acetylamino)-methyl]-phenyl}-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester

: 1314641-64-9
3-{2-fluoro-5-[(2,2,2-trifluoro-acetylamino)-methyl]-phenyl}-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Guidance literature:: With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 9h; under 3102.97 Torr;
DOI:10.1016/j.bmcl.2011.12.127