5-bromo-1-(4-tert-butoxycarbonyloxy-cyclopent-2-enyl)-1H-pyrrole-2-carboxylic acid

Base Information

• Chemical Name: 5-bromo-1-(4-tert-butoxycarbonyloxy-cyclopent-2-enyl)-1H-pyrrole-2-carboxylic acid
• CAS No.: 890122-54-0
• Molecular Formula: C₁₅H₁₈BrNO₅
• Molecular Weight: 372.216
• Mol file: 890122-54-0.mol

Synonyms:5-bromo-1-(4-tert-butoxycarbonyloxy-cyclopent-2-enyl)-1H-pyrrole-2-carboxylic acid

Chemical Property of 5-bromo-1-(4-tert-butoxycarbonyloxy-cyclopent-2-enyl)-1H-pyrrole-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-bromo-1-(4-tert-butoxycarbonyloxy-cyclopent-2-enyl)-1H-pyrrole-2-carboxylic acid

There total 1 articles about 5-bromo-1-(4-tert-butoxycarbonyloxy-cyclopent-2-enyl)-1H-pyrrole-2-carboxylic acid 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: 86.0%

5-bromo-1-(4-tert-butoxycarbonyloxy-cyclopent-2-enyl)-1H-pyrrole-2-carboxylic acid methyl ester (890122-44-8) → 5-bromo-1-(4-tert-butoxycarbonyloxy-cyclopent-2-enyl)-1H-pyrrole-2-carboxylic acid (890122-54-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 48h;

DOI:10.1021/ja061105q

Reference yield:

5-bromo-1-(4-tert-butoxycarbonyloxy-cyclopent-2-enyl)-1H-pyrrole-2-carboxylic acid (890122-54-0) → N-(8-bromo-4-methoxy-2,5-dioxo-2,3,3a,4,5,8b-hexahydro-1H-4,8a-diaza-as-indacen-3-yl)-4-methyl-benzenesulfonamide (890122-51-7)

Guidance literature:

Multi-step reaction with 6 steps

1: (COCl)2 / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

2: 87.7 mg / K₂CO₃ / H₂O; tetrahydrofuran; dimethylformamide / 12 h / 20 °C

3: 91.5 percent / (R,R)-1,2-bis(2'-Ph₂PPhCONH)cyclohexane; Cs₂CO₃ / Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 12 h / 20 °C

4: 52 percent / 4 Angstroem molecular sieves / N,N'-bis(2',6'-iPr₂Ph)-c-(N-CH=CH-N)C=CuCl / benzene / 4 h / 20 °C

5: 84 percent / TFA / dioxane; H₂O / 2.5 h / 150 °C / microwave irradiation

6: 80 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

With oxalyl dichloride; 4 A molecular sieve; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; Dess-Martin periodane; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; trifluoroacetic acid; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; benzene; 6: Dess-Martin oxidation;

DOI:10.1021/ja061105q

Reference yield:

5-bromo-1-(4-tert-butoxycarbonyloxy-cyclopent-2-enyl)-1H-pyrrole-2-carboxylic acid (890122-54-0) → (5aS,5bR,8aR,9aS)-1-Bromo-8a-hydroxy-5-methoxy-8-methyl-6-(toluene-4-sulfonyl)-5,5a,5b,6,8,8a,9,9a-octahydro-5,6,8,9b-tetraaza-cyclopenta[b]-as-indacene-4,7-dione (890122-52-8)

Guidance literature:

Multi-step reaction with 7 steps

1: (COCl)2 / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

2: 87.7 mg / K₂CO₃ / H₂O; tetrahydrofuran; dimethylformamide / 12 h / 20 °C

3: 91.5 percent / (R,R)-1,2-bis(2'-Ph₂PPhCONH)cyclohexane; Cs₂CO₃ / Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 12 h / 20 °C

4: 52 percent / 4 Angstroem molecular sieves / N,N'-bis(2',6'-iPr₂Ph)-c-(N-CH=CH-N)C=CuCl / benzene / 4 h / 20 °C

5: 84 percent / TFA / dioxane; H₂O / 2.5 h / 150 °C / microwave irradiation

6: 80 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

7: 53 percent / Cs₂CO₃ / CH₂Cl₂; benzene / 4 h / 20 °C

With oxalyl dichloride; 4 A molecular sieve; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; Dess-Martin periodane; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; trifluoroacetic acid; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; benzene; 6: Dess-Martin oxidation;

DOI:10.1021/ja061105q

upstream raw materials:

5-bromo-1-(4-tert-butoxycarbonyloxy-cyclopent-2-enyl)-1H-pyrrole-2-carboxylic acid methyl ester

Downstream raw materials:

1-bromo-5-methoxy-6-(toluene-4-sulfonyl)-5a,5b,6,6a,7,7a-hexahydro-5H-5,6,7b-triaza-cyclopropa[b]-as-indacen-4-one

N-(8-bromo-2-hydroxy-4-methoxy-5-oxo-2,3,3a,4,5,8b-hexahydro-1H-4,8a-diaza-as-indacen-3-yl)-4-methyl-benzenesulfonamide

N-(8-bromo-4-methoxy-2,5-dioxo-2,3,3a,4,5,8b-hexahydro-1H-4,8a-diaza-as-indacen-3-yl)-4-methyl-benzenesulfonamide

(5aS,5bR,8aR,9aS)-1-Bromo-8a-hydroxy-5-methoxy-8-methyl-6-(toluene-4-sulfonyl)-5,5a,5b,6,8,8a,9,9a-octahydro-5,6,8,9b-tetraaza-cyclopenta[b]-as-indacene-4,7-dione