7-Oxabicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid, 1,4-dimethyl-3-[[(phenylmethyl)amino]carbonyl]-, 1-methylethyl ester, (1R,4S)-

Base Information

• Chemical Name: 7-Oxabicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid, 1,4-dimethyl-3-[[(phenylmethyl)amino]carbonyl]-, 1-methylethyl ester, (1R,4S)-
• CAS No.: 877822-59-8
• Molecular Formula: C20H23NO4
• Molecular Weight: 341.407
• Mol file: 877822-59-8.mol

Synonyms:

Chemical Property of 7-Oxabicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid, 1,4-dimethyl-3-[[(phenylmethyl)amino]carbonyl]-, 1-methylethyl ester, (1R,4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-Oxabicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid, 1,4-dimethyl-3-[[(phenylmethyl)amino]carbonyl]-, 1-methylethyl ester, (1R,4S)-

There total 5 articles about 7-Oxabicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid, 1,4-dimethyl-3-[[(phenylmethyl)amino]carbonyl]-, 1-methylethyl ester, (1R,4S)- 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:

(1R,4S)-1,4-Dimethyl-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid monoisopropyl ester + benzylamine (100-46-9) → (1R,4S)-3-Benzylcarbamoyl-1,4-dimethyl-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid isopropyl ester (877822-59-8)

Guidance literature:

With triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; for 3h;

DOI:10.1002/anie.200503374

Reference yield:

(1S,4R)-1,4-Dimethyl-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid monomethyl ester (877822-56-5) → (1R,4S)-3-Benzylcarbamoyl-1,4-dimethyl-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid isopropyl ester (877822-59-8)

Guidance literature:

Multi-step reaction with 3 steps

1: DMAP; DMT-MM / 3 h / 50 °C

2: LiOH / tetrahydrofuran; H₂O / 2 h / 20 °C

3: DMT-MM / tetrahydrofuran / 3 h / 20 °C

With dmap; lithium hydroxide; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; water;

DOI:10.1021/ja069035a

Reference yield:

(1R,4S)-1,4-Dimethyl-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid 2-isopropyl ester 3-methyl ester → (1R,4S)-3-Benzylcarbamoyl-1,4-dimethyl-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid isopropyl ester (877822-59-8)

Guidance literature:

Multi-step reaction with 2 steps

1: LiOH / tetrahydrofuran; H₂O / 2 h / 20 °C

2: DMT-MM / tetrahydrofuran / 3 h / 20 °C

With lithium hydroxide; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; water;

DOI:10.1021/ja069035a

upstream raw materials:

benzylamine

2,5-dimethylfuran

(1S,4R)-1,4-Dimethyl-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid monomethyl ester

dimethyl 1,4-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

Downstream raw materials:

(1S,2R,3S,4S)-2,3-Diacetyl-4-benzylcarbamoyl-cyclobutanecarboxylic acid isopropyl ester