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

Base Information

• Chemical Name: (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-isopropylpentanoate
• CAS No.: 154520-27-1
• Molecular Formula: C₃₁H₅₆N₂O₄S
• Molecular Weight: 552.863
• Mol file: 154520-27-1.mol

Synonyms:(2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-isopropylpentanoate

Chemical Property of (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-isopropylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-isopropylpentanoate

There total 4 articles about (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-isopropylpentanoate 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%

(2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate (154520-17-9) → (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-isopropylpentanoate (154520-27-1)

Guidance literature:

With hydrogen; rhodium on alumina; In ethanol; ammonia; at 35 ℃; for 24h;

DOI:10.1021/jo00088a034

Reference yield:

2-Cyano-3-methylbutanoyl chloride (98134-33-9) → (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-isopropylpentanoate (154520-27-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / AgCN / toluene / 4 h / 80 °C

2: 63 percent / LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, HMPA, -78 deg C to r.t.; r.t., 1 d

3: 87 percent / H₂ / 5percent Rh-Al₂O₃ / ethanol; NH₃ / 24 h / 35 °C

With silver cyanide; hydrogen; lithium diisopropyl amide; rhodium on alumina; In ethanol; ammonia; toluene;

DOI:10.1021/jo00088a034

Reference yield:

2-Cyano-3-methylbutanoic acid (22426-27-3) → (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-isopropylpentanoate (154520-27-1)

Guidance literature:

Multi-step reaction with 4 steps

1: PCl₅

2: 89 percent / AgCN / toluene / 4 h / 80 °C

3: 63 percent / LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, HMPA, -78 deg C to r.t.; r.t., 1 d

4: 87 percent / H₂ / 5percent Rh-Al₂O₃ / ethanol; NH₃ / 24 h / 35 °C

With silver cyanide; phosphorus pentachloride; hydrogen; lithium diisopropyl amide; rhodium on alumina; In ethanol; ammonia; toluene;

DOI:10.1021/jo00088a034

upstream raw materials:

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

2-Cyano-3-methylbutanoic acid

2-Cyano-3-methylbutanoyl chloride

(2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-methyl-2-cyanobutanoate

Downstream raw materials:

(3R)-3-Isopropyl-3-propyl-2-azetidinone