(1S,2S,3R)-3-Hydroxy-2-methoxycarbonylamino-cyclohexanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2S,3R)-3-Hydroxy-2-methoxycarbonylamino-cyclohexanecarboxylic acid methyl ester
• CAS No.: 220431-78-7
• Molecular Formula: C₁₀H₁₇NO₅
• Molecular Weight: 231.249
• Mol file: 220431-78-7.mol

Synonyms:(1S,2S,3R)-3-Hydroxy-2-methoxycarbonylamino-cyclohexanecarboxylic acid methyl ester

Chemical Property of (1S,2S,3R)-3-Hydroxy-2-methoxycarbonylamino-cyclohexanecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R)-3-Hydroxy-2-methoxycarbonylamino-cyclohexanecarboxylic acid methyl ester

There total 3 articles about (1S,2S,3R)-3-Hydroxy-2-methoxycarbonylamino-cyclohexanecarboxylic 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: 87.0%

(5R,6S)-5-Hydroxy-6-methoxycarbonylamino-cyclohex-1-enecarboxylic acid methyl ester (220431-77-6) → (1S,2S,3R)-3-Hydroxy-2-methoxycarbonylamino-cyclohexanecarboxylic acid methyl ester (220431-78-7)

Guidance literature:

With hydrogen; 10% palladium on active carbon; In ethanol; ethyl acetate; for 144h; under 2475.2 Torr;

DOI:10.1055/s-1999-2539

Reference yield:

(1S,2R,3S,4R)-3-Azidocarbonyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (220431-75-4) → (1S,2S,3R)-3-Hydroxy-2-methoxycarbonylamino-cyclohexanecarboxylic acid methyl ester (220431-78-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) toluene, reflux, 3 h, 2.) toluene, reflux, 2 h

2: 41 percent / LiHDMS / tetrahydrofuran; hexane / 2 h / -10 °C

3: 87 percent / H₂ / 10percentPd/C / ethanol; ethyl acetate / 144 h / 2475.2 Torr

With hydrogen; lithium hexamethyldisilazane; 10% palladium on active carbon; In tetrahydrofuran; ethanol; hexane; ethyl acetate;

DOI:10.1055/s-1999-2539

Reference yield:

(1S,2R,3S,4R)-3-Methoxycarbonylamino-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (220431-76-5) → (1S,2S,3R)-3-Hydroxy-2-methoxycarbonylamino-cyclohexanecarboxylic acid methyl ester (220431-78-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / LiHDMS / tetrahydrofuran; hexane / 2 h / -10 °C

2: 87 percent / H₂ / 10percentPd/C / ethanol; ethyl acetate / 144 h / 2475.2 Torr

With hydrogen; lithium hexamethyldisilazane; 10% palladium on active carbon; In tetrahydrofuran; ethanol; hexane; ethyl acetate;

DOI:10.1055/s-1999-2539

upstream raw materials:

(5R,6S)-5-Hydroxy-6-methoxycarbonylamino-cyclohex-1-enecarboxylic acid methyl ester

(1S,2R,3S,4R)-3-Azidocarbonyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

(1S,2R,3S,4R)-3-Methoxycarbonylamino-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester