trans-4-Cyclohexyl-L-proline hydrochloride

Base Information

• Chemical Name: trans-4-Cyclohexyl-L-proline hydrochloride
• CAS No.: 90657-55-9
• Molecular Formula: C11H20ClNO2
• Molecular Weight: 233.738
• Hs Code.: 2933990090
• European Community (EC) Number: 419-160-1,618-614-8
• DSSTox Substance ID: DTXSID90510300
• Mol file: 90657-55-9.mol

Synonyms:90657-55-9;trans-4-Cyclohexyl-L-proline hydrochloride;H-Chpro-OH.HCl;(2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid hydrochloride;(4S)-4-Cyclohexyl-L-proline Hydrochloride;Trans-4-cyclohexyl-l-proline, HCl;(2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid;hydrochloride;trans-4-cyclohexyl proline hcl;TRANS-4-CYCLOHEXYL-L-PROLINE HCL;L-Proline, 4-cyclohexyl-, hydrochloride, (4S)-;trans-4-cyclohexyl-L-proline monohydrochloride;EC 419-160-1;SCHEMBL3418559;DTXSID90510300;BHGFUQJUTOVQOS-UXQCFNEQSA-N;MFCD08704794;AKOS015843984;AKOS015898070;AC-6231;CS-W006093;GS-3299;HY-W006093;(trans)-4-cyclohexyl-L-proline hydrochloride;NS00078730;(4S)-4-Cyclohexyl-L-proline hydrochloride (1:1);J-525020;(4S)-4-Cyclohexyl-L-proline--hydrogen chloride (1/1);(4S)-4-Cyclohexyl-L-proline hydrochloride 100 microg/mL in Acetonitrile

Chemical Property of trans-4-Cyclohexyl-L-proline hydrochloride

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 257-267 °C
• PSA: 49.33000
• LogP: 2.76020
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 233.1182566
• Heavy Atom Count: 15
• Complexity: 211

Purity/Quality:

99.9% ^*data from raw suppliers

(4S)-4-Cyclohexyl-L-prolineHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-38-41-43-62
• Safety Statements: 22-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C2CC(NC2)C(=O)O.Cl
• Isomeric SMILES: C1CCC(CC1)[C@@H]2C[C@H](NC2)C(=O)O.Cl
• Uses: It is an intermediate for the synthesis of angiotensin-converting enzyme inhibitors, e.g. Fosinopril (F727800).

Technology Process of trans-4-Cyclohexyl-L-proline hydrochloride

There total 2 articles about trans-4-Cyclohexyl-L-proline hydrochloride 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: 91.0%

(2S,4S)-4-phenylpyrrolidine-2-carboxylic acid → trans-4-cyclohexyl-L-proline hydrochloride (90657-55-9)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol;

DOI:10.1021/jm00401a014

Reference yield:

trimethylsilyl cyanide (7677-24-9) + (S)-4-Cyclohexyl-2-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (210585-86-7) → trans-4-cyclohexyl-L-proline hydrochloride (90657-55-9) + (2R,4S)-4-Cyclohexyl-pyrrolidine-2-carboxylic acid; hydrochloride

Guidance literature:

With hydrogenchloride; boron trifluoride diethyl etherate; Yield given. Multistep reaction; 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) reflux, 22 h;

DOI:10.1021/jo971540q

Reference yield: 100.0%

ethanol (64-17-5) + trans-4-cyclohexyl-L-proline hydrochloride (90657-55-9) → (2S,4S)-ethyl 4-cyclohexylpyrrolidine-2-carboxylate hydrochloride

Guidance literature:

With thionyl chloride; at 0 - 20 ℃; for 16h;

upstream raw materials:

trimethylsilyl cyanide

(S)-4-Cyclohexyl-2-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

trans-4-cyclohexyl-L-prolinol

(2S-trans)-1-[(benzyloxy)carbonyl]-4-cyclohexyl-2-pyrrolidinemethanol

(2S,4S)-4-Cyclohexyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

(2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid

Refernces

• 1、 Krapcho,Turk,Cushman,Powell,DeForrest,Spitzmiller,Karanewsky,Duggan,Rovnvak,Schwartz,Natarajan,Godfrey,Ryono,Neubeck,Atwa,Petrillo Jr.. "Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines". . p. 1148 - 1160. Retrieved 2007/10/02.