trans-4-Cyclohexyl-L-proline

Base Information

• Chemical Name: trans-4-Cyclohexyl-L-proline
• CAS No.: 103201-78-1
• Molecular Formula: C11H19NO2
• Molecular Weight: 197.277
• Hs Code.: 2933990090
• European Community (EC) Number: 600-406-3
• DSSTox Substance ID: DTXSID70431160
• Nikkaji Number: J1.756.714D
• ChEMBL ID: CHEMBL4091905
• Mol file: 103201-78-1.mol

Synonyms:trans-4-Cyclohexyl-L-proline;103201-78-1;(2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid;130092-20-5;H-Chpro-OH;L-Proline, 4-cyclohexyl-, (4S)-;(4S)-4-cyclohexyl-L-proline;(2S,4S)-4-Cyclohexyl-pyrrolidine-2-carboxylic acid;EC 600-406-3;MFCD08061929;trans-4-cyclohexylpyrrolidine-2-carboxylic acid;4beta-Cyclohexyl-L-proline;SCHEMBL2238814;CHEMBL4091905;(trans)-4-Cyclohexyl-L-proline;DTXSID70431160;XRZWVSXEDRYQGC-ZJUUUORDSA-N;AC8034;AKOS006287624;AKOS015840728;AC-7636;DS-13893;CS-0042526;EN300-91503;trans-4-cyclohexylpyrrolidine-2-carboxylicacid;A800690;Q-102535;Q27464420;Z1198175867;4-cyclohexylpyrrolidine-2-carboxylic acid

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 260-262 °C(Solv: methanol (67-56-1); ethyl ether (60-29-7))
• Refractive Index: 1.517
• Boiling Point: 343.919 °C at 760 mmHg
• PKA: 2.35±0.40(Predicted)
• Flash Point: 161.797 °C
• PSA: 49.33000
• Density: 1.114 g/cm³
• LogP: 1.95820
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 197.141578849
• Heavy Atom Count: 14
• Complexity: 211

Purity/Quality:

99% ^*data from raw suppliers

trans-4-Cyclohexyl-L-proline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C2CC(NC2)C(=O)O
• Isomeric SMILES: C1CCC(CC1)[C@@H]2C[C@H](NC2)C(=O)O

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

There total 28 articles about trans-4-Cyclohexyl-L-proline 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: 90.0%

trans-4-phenyl-L-proline (96314-26-0) → (2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid (103201-78-1,130092-20-5)

Guidance literature:

With hydrogenchloride; 5% rhodium-on-charcoal; hydrogen; In methanol; at 30 ℃; for 2h; under 15001.5 Torr;

Reference yield: 35.0%

benzyl trans-4-cyclohexyl-5-thio-N-benzyl-L-pyroglutamate (438492-63-8) → (2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid (103201-78-1,130092-20-5)

Guidance literature:

benzyl trans-4-cyclohexyl-5-thio-N-benzyl-L-pyroglutamate; With water; nickel; In ethanol; for 1.5h; Heating;

With hydrogen; acetic acid; palladium on activated charcoal; In methanol; at 50 ℃; for 2h; under 15200 Torr;

DOI:10.1016/S0957-4166(02)00052-6

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid (103201-78-1,130092-20-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / TosOH / toluene / 9 h / Heating

2: 1.) LDA, / 1.) THF, -78 deg C, 30 min, 2.) THF, -20 deg C, 20 min

3: 100 percent / LAH / tetrahydrofuran / 1 h / Heating

4: 65 percent / H₂ / 10percentPd/C / ethyl acetate; acetic acid / 2 h / 2327.2 Torr

5: 77.9 g / aq.K₂CO₃ / tetrahydrofuran / 0.25 h / 0 °C

6: 78.4 g / aq.(CrO₃/H₂SO₄) / acetone / 3 h / -5 °C

7: 86.3 percent / H₂ / 10percentPd/C / methanol / 2 h / 760 Torr / Ambient temperature

With chromium(VI) oxide; lithium aluminium tetrahydride; sulfuric acid; hydrogen; potassium carbonate; toluene-4-sulfonic acid; lithium diisopropyl amide; 10% palladium on active carbon; In tetrahydrofuran; methanol; acetic acid; ethyl acetate; acetone; toluene;

DOI:10.1021/jo00366a011

upstream raw materials:

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

benzyl trans-4-cyclohexyl-5-thio-N-benzyl-L-pyroglutamate

N-benzyl-L-pyroglutamic acid

rac-3-bromocyclohexene

Downstream raw materials:

Fosinoprilat

fosinopril

Refernces

• 1、 Liu, Ri-Long,Yan, Yun-Yun,Zhang, Ting,Zhang, Xue-Jing,Yan, Ming. "A practical synthesis of optically active δ-nitro-α-ketoesters and 4-cyclohexyl-proline catalyzed by chiral squamides". . p. 1416 - 1422. Retrieved 2015/12/09.
• 2、 Thottathil, John K.,Moniot, Jerome L.,Mueller, Richard H.,Wong, Michael K. Y.,Kissick, Thomas P.. "Conversion of L-Pyroglutamic Acid to 4-Alkyl-Substituted L-Prolines. The Synthesis of trans-4-Cyclohexyl-L-proline". . p. 3140 - 3143. Retrieved 2007/10/02.