1-Pyrrolidinecarboxylic acid, 4-(dicyclohexylphosphino)-2-[(dicyclohexylphosphino)methyl]-, 1,1-dimethylethyl ester, (2S-cis)-

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 4-(dicyclohexylphosphino)-2-[(dicyclohexylphosphino)methyl]-, 1,1-dimethylethyl ester, (2S-cis)-
• CAS No.: 110466-08-5
• Molecular Formula: C₃₄H₆₁NO₂P₂
• Molecular Weight: 577.811
• DSSTox Substance ID: DTXSID00274249
• Wikidata: Q81977461
• Mol file: 110466-08-5.mol

Synonyms:Bccp;DTXSID00274249;1-Pyrrolidinecarboxylic acid, 4-(dicyclohexylphosphino)-2-[(dicyclohexylphosphino)methyl]-, 1,1-dimethylethyl ester, (2S-cis)-;110466-08-5

Chemical Property of 1-Pyrrolidinecarboxylic acid, 4-(dicyclohexylphosphino)-2-[(dicyclohexylphosphino)methyl]-, 1,1-dimethylethyl ester, (2S-cis)-

Chemical Property:

• XLogP3: 8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 577.41775418
• Heavy Atom Count: 39
• Complexity: 709

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1CP(C2CCCCC2)C3CCCCC3)P(C4CCCCC4)C5CCCCC5
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@H]1CP(C2CCCCC2)C3CCCCC3)P(C4CCCCC4)C5CCCCC5

Technology Process of 1-Pyrrolidinecarboxylic acid, 4-(dicyclohexylphosphino)-2-[(dicyclohexylphosphino)methyl]-, 1,1-dimethylethyl ester, (2S-cis)-

There total 4 articles about 1-Pyrrolidinecarboxylic acid, 4-(dicyclohexylphosphino)-2-[(dicyclohexylphosphino)methyl]-, 1,1-dimethylethyl ester, (2S-cis)- 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:

(2S,4S)-N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine (61478-28-2) → (2S-cis)-4-(dicyclohexylphosphino)-2-<(dicyclohexylphosphino)methyl>-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester (110466-08-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / 10percent aq. H₂O₂ / acetone

2: 98 percent / 3percent HCl / methanol

3: 91 percent / H₂, 5percent Rh on Al₂O₃ / methanol

4: HSiCl₃, Et₃N / acetonitrile / 3 h / Heating

5: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

With hydrogenchloride; rhodium on alumina; trichlorosilane; hydrogen; dihydrogen peroxide; triethylamine; In methanol; dichloromethane; acetone; acetonitrile;

DOI:10.1248/cpb.42.481

Reference yield:

(2S,3S)-N-(t-butoxycarbonyl)-4-diphenylphosphinyl-2-diphenylphosphinylmethylpyrrolidine (96332-73-9) → (2S-cis)-4-(dicyclohexylphosphino)-2-<(dicyclohexylphosphino)methyl>-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester (110466-08-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / 3percent HCl / methanol

2: 91 percent / H₂, 5percent Rh on Al₂O₃ / methanol

3: HSiCl₃, Et₃N / acetonitrile / 3 h / Heating

4: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

With hydrogenchloride; rhodium on alumina; trichlorosilane; hydrogen; triethylamine; In methanol; dichloromethane; acetonitrile;

DOI:10.1248/cpb.42.481

Reference yield:

(2S,4S)-4-(Diphenyl-phosphinoyl)-2-(diphenyl-phosphinoylmethyl)-pyrrolidine; hydrochloride → (2S-cis)-4-(dicyclohexylphosphino)-2-<(dicyclohexylphosphino)methyl>-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester (110466-08-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / H₂, 5percent Rh on Al₂O₃ / methanol

2: HSiCl₃, Et₃N / acetonitrile / 3 h / Heating

3: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

With rhodium on alumina; trichlorosilane; hydrogen; triethylamine; In methanol; dichloromethane; acetonitrile;

DOI:10.1248/cpb.42.481

upstream raw materials:

di-tert-butyl dicarbonate

(2S,3S)-4-dicyclohexylphosphinyl-2-dicyclohexylphosphinylmethylpyrrolidine

(2S,4S)-N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine

(2S,3S)-N-(t-butoxycarbonyl)-4-diphenylphosphinyl-2-diphenylphosphinylmethylpyrrolidine

Refernces

• 1、 Morimoto, Toshiaki,Takahashi, Hisashi,Fujii, Katsuyasu,Chiba, Mitsuo,Achiwa, Kazuo. "Synthesis of a New Chiral Pyrrolidine Ligand Bearing Two Different Types of Phosphino Groups and Their Effects on the Asymmetric Hydrogenation of Ketopantalolactone". . p. 2061 - 2064. Retrieved 2007/10/02.