(2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methylbutanoate

Base Information

• Chemical Name: (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methylbutanoate
• CAS No.: 154520-13-5
• Molecular Formula: C₂₈H₄₆N₂O₄S
• Molecular Weight: 506.75
• Mol file: 154520-13-5.mol

Synonyms:(2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methylbutanoate

Chemical Property of (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methylbutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methylbutanoate

There total 4 articles about (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methylbutanoate 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: 52.0%

(2RS)-(1'S,2'R,4'R)-10'-(dicyclohexylsulfamoyl)isobornyl-2-cyanobutanoate (610784-26-4) + methyl iodide (74-88-4) → (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methylbutanoate (154520-13-5) + (2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methylbutanoate

Guidance literature:

With lithium diisopropyl amide; Yields of byproduct given; 1.) THF, -78 deg C, 1 h, 2.) THF, HMPA, -78 deg C to r.t.; r.t., 1 d;

DOI:10.1021/jo00088a034

Reference yield:

1-cyano-propane-1-carboxylic acid (51789-75-4) → (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methylbutanoate (154520-13-5)

Guidance literature:

Multi-step reaction with 3 steps

1: PCl₅

2: 91 percent / AgCN / toluene / 4 h / 80 °C

3: 52 percent / LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, HMPA, -78 deg C to r.t.; r.t., 1 d

With silver cyanide; phosphorus pentachloride; lithium diisopropyl amide; In toluene;

DOI:10.1021/jo00088a034

Reference yield:

2-Cyanobutanoyl chloride (57244-09-4) → (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methylbutanoate (154520-13-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / AgCN / toluene / 4 h / 80 °C

2: 52 percent / LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, HMPA, -78 deg C to r.t.; r.t., 1 d

With silver cyanide; lithium diisopropyl amide; In toluene;

DOI:10.1021/jo00088a034

upstream raw materials:

ethyl iodide

(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate

(2RS)-(1'S,2'R,4'R)-10'-(dicyclohexylsulfamoyl)isobornyl-2-cyanobutanoate

methyl iodide

Downstream raw materials:

(2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-methylbutanoate