(1R,3S)-3-Benzyloxycarbonylmethyl-cyclopentanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1R,3S)-3-Benzyloxycarbonylmethyl-cyclopentanecarboxylic acid methyl ester
• CAS No.: 194989-16-7
• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.332
• Mol file: 194989-16-7.mol

Synonyms:(1R,3S)-3-Benzyloxycarbonylmethyl-cyclopentanecarboxylic acid methyl ester

Chemical Property of (1R,3S)-3-Benzyloxycarbonylmethyl-cyclopentanecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (1R,3S)-3-Benzyloxycarbonylmethyl-cyclopentanecarboxylic acid methyl ester

There total 2 articles about (1R,3S)-3-Benzyloxycarbonylmethyl-cyclopentanecarboxylic acid methyl 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:

(+)-cis-(1S,3R)-3-carbomethoxycyclopentane carboxylic acid (96443-42-4) → (1R,3S)-3-Benzyloxycarbonylmethyl-cyclopentanecarboxylic acid methyl ester (194989-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2, DMF / CH₂Cl₂ / 2.5 h / Ambient temperature

2: 2.) 2,4,6-trimethylpyridine / 1.) THF, acetonitrile, 0 deg C, 10 h, 2.) 180 deg C to 185 deg C, 7 min

With 2,4,6-trimethyl-pyridine; oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1021/ja963708f

Reference yield:

(1R,3S)-3-Chlorocarbonyl-cyclopentanecarboxylic acid methyl ester + benzyl alcohol (100-51-6,185532-71-2) + diazomethyl-trimethyl-silane (18107-18-1) → (1R,3S)-3-Benzyloxycarbonylmethyl-cyclopentanecarboxylic acid methyl ester (194989-16-7)

Guidance literature:

With 2,4,6-trimethyl-pyridine; Yield given. Multistep reaction; 1.) THF, acetonitrile, 0 deg C, 10 h, 2.) 180 deg C to 185 deg C, 7 min;

DOI:10.1021/ja963708f

Reference yield:

(1R,3S)-3-Benzyloxycarbonylmethyl-cyclopentanecarboxylic acid methyl ester (194989-16-7) → (1S,3S)-3-(4-Nitro-phenoxycarbonylmethyl)-cyclopentanecarboxylic acid

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaOH, 2.) aq. HCl / 1.) dioxane, 24 h, rt, 2.) 180 deg C, 6 h

2: 30 percent / DCC, 1-hydroxybenzotriazole monohydrate / ethyl acetate / 24 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In ethyl acetate;

DOI:10.1021/ja963708f

upstream raw materials:

benzyl alcohol

diazomethyl-trimethyl-silane

(+)-cis-(1S,3R)-3-carbomethoxycyclopentane carboxylic acid