(1R,2R,4R)-2-(methoxycarbonyl)-4-[(4-nitrobenzoyl)oxy]cyclopentanecarboxylic acid

Base Information

• Chemical Name: (1R,2R,4R)-2-(methoxycarbonyl)-4-[(4-nitrobenzoyl)oxy]cyclopentanecarboxylic acid
• CAS No.: 1333964-98-9
• Molecular Formula: C₁₅H₁₅NO₈
• Molecular Weight: 337.286
• Mol file: 1333964-98-9.mol

Synonyms:(1R,2R,4R)-2-(methoxycarbonyl)-4-[(4-nitrobenzoyl)oxy]cyclopentanecarboxylic acid

Chemical Property of (1R,2R,4R)-2-(methoxycarbonyl)-4-[(4-nitrobenzoyl)oxy]cyclopentanecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,4R)-2-(methoxycarbonyl)-4-[(4-nitrobenzoyl)oxy]cyclopentanecarboxylic acid

There total 6 articles about (1R,2R,4R)-2-(methoxycarbonyl)-4-[(4-nitrobenzoyl)oxy]cyclopentanecarboxylic 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:

benzyl methyl (1R,2R,4S)-4-[(4-nitro-benzoyl)oxy]-1,2-cyclopentanedicarboxylate (1333964-95-6) → (1R,2R,4R)-2-(methoxycarbonyl)-4-[(4-nitrobenzoyl)oxy]cyclopentanecarboxylic acid (1333964-98-9)

Guidance literature:

benzyl methyl (1R,2R,4S)-4-[(4-nitro-benzoyl)oxy]-1,2-cyclopentanedicarboxylate; With sodium formate; palladium diacetate; In N,N-dimethyl-formamide; at 100 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In water; N,N-dimethyl-formamide; at 22 ℃; pH=1;

Reference yield:

racemic trans-cyclopentanone-3,4-dicarboxylic acid (1703-61-3,3128-17-4,3128-18-5,67885-97-6) → (1R,2R,4R)-2-(methoxycarbonyl)-4-[(4-nitrobenzoyl)oxy]cyclopentanecarboxylic acid (1333964-98-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: water; methanol / 0.25 h / 40 °C / Reflux

2.1: ammonium hydroxide / water / 0.5 h / 80 °C

2.2: 2 h / Reflux

3.1: hydrogen / 5 percent rhodium on alumina / tetrahydrofuran

4.1: sodium carbonate / toluene / 6 h / Inert atmosphere; Reflux

5.1: triphenylphosphine / toluene / 0.5 h / Reflux; Dean-Stark apparatus

5.2: 13 h / -5 - 22 °C

6.1: sodium formate / palladium diacetate / N,N-dimethyl-formamide / 3 h / 100 °C / Inert atmosphere

6.2: 22 °C / pH 1

With ammonium hydroxide; hydrogen; sodium formate; sodium carbonate; triphenylphosphine; palladium diacetate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; toluene;

Reference yield:

trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane (35079-19-7) → (1R,2R,4R)-2-(methoxycarbonyl)-4-[(4-nitrobenzoyl)oxy]cyclopentanecarboxylic acid (1333964-98-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogen / 5 percent rhodium on alumina / tetrahydrofuran

2.1: sodium carbonate / toluene / 6 h / Inert atmosphere; Reflux

3.1: triphenylphosphine / toluene / 0.5 h / Reflux; Dean-Stark apparatus

3.2: 13 h / -5 - 22 °C

4.1: sodium formate / palladium diacetate / N,N-dimethyl-formamide / 3 h / 100 °C / Inert atmosphere

4.2: 22 °C / pH 1

With hydrogen; sodium formate; sodium carbonate; triphenylphosphine; palladium diacetate; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

upstream raw materials:

trans-(3R,4R)-3,4-bis(methoxycarbonyl)cyclopentanol

racemic trans-cyclopentanone-3,4-dicarboxylic acid

trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane

benzyl methyl (1R,2R,4R)-4-hydroxy-1,2-cyclopentanedicarboxylate

Downstream raw materials:

methyl (1R,2R,4S)-2-[5-hexen-1-yl(methyl)carbamoyl]-4-[[2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxy-8-methyl-4-quinolinyl]oxy]cyclopentanecarboxylate