(1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid (2-hydroxy-phenyl)-amide

Base Information

• Chemical Name: (1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid (2-hydroxy-phenyl)-amide
• CAS No.: 127498-24-2
• Molecular Formula: C₁₆H₁₉NO₃
• Molecular Weight: 273.332
• Mol file: 127498-24-2.mol

Synonyms:(1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid (2-hydroxy-phenyl)-amide

Chemical Property of (1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid (2-hydroxy-phenyl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid (2-hydroxy-phenyl)-amide

There total 2 articles about (1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid (2-hydroxy-phenyl)-amide 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: 80.0%

ketopinic acid chloride (54371-12-9,66884-33-1,66965-39-7,86023-72-5) + 2-amino-phenol (95-55-6) → (1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid (2-hydroxy-phenyl)-amide (127498-24-2)

Guidance literature:

With triethylamine; In dichloromethane; 1.) 0 deg C, 15 min; 2.) RT, 4 h;

DOI:10.1016/0040-4020(94)01059-9

Reference yield:

(1S)-(+)-ketopinic acid (464-78-8,6994-94-1,64234-14-6,40724-67-2) → (1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid (2-hydroxy-phenyl)-amide (127498-24-2)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / 5 h / 80 °C

2: 80 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 15 min; 2.) RT, 4 h

With thionyl chloride; triethylamine; In dichloromethane;

DOI:10.1016/0040-4020(94)01059-9

Reference yield: 90.0%

aminomethylphosphonic acid diethyl ester (50917-72-1) + (1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid (2-hydroxy-phenyl)-amide (127498-24-2) → {[(1S,4R)-1-(2-Hydroxy-phenylcarbamoyl)-7,7-dimethyl-bicyclo[2.2.1]hept-(2E)-ylideneamino]-methyl}-phosphonic acid diethyl ester (144757-96-0)

Guidance literature:

With boron trifluoride; In toluene;

DOI:10.1016/S0957-4166(00)82094-7

upstream raw materials:

ketopinic acid chloride

2-amino-phenol

(1S)-(+)-ketopinic acid

Downstream raw materials:

{[(1S,4R)-1-(2-Hydroxy-phenylcarbamoyl)-7,7-dimethyl-bicyclo[2.2.1]hept-(2E)-ylideneamino]-methyl}-phosphonic acid diethyl ester

10-(N-o-hydroxyphenylamide)-N-benzyl-7,7-dimethyl-dicyclo-<2,2,1>-heptane-2-imine

(1S,4R)-7,7-Dimethyl-2-[(E)-(R)-1-phenyl-ethylimino]-bicyclo[2.2.1]heptane-1-carboxylic acid (2-hydroxy-phenyl)-amide

(1S,4R)-7,7-Dimethyl-2-[(E)-(R)-2-methyl-1-phenyl-propylimino]-bicyclo[2.2.1]heptane-1-carboxylic acid (2-hydroxy-phenyl)-amide