CID 11806790

Base Information

• Chemical Name: CID 11806790
• CAS No.: 16652-71-4
• Molecular Formula: C12H15NO2^.ClH
• Molecular Weight: 241.718
• Hs Code.: 29339900
• Mol file: 16652-71-4.mol

Synonyms:

Chemical Property of CID 11806790

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0.000659mmHg at 25°C
• Melting Point: 148-151 °C(lit.)
• Refractive Index: 1.4365
• Boiling Point: 309 °C at 760 mmHg
• Flash Point: 140.7 °C
• PSA: 38.33000
• Density: 1.121g/cm3
• LogP: 2.61260
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: soluble in Methanol
• Water Solubility.: miscible
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 241.0869564
• Heavy Atom Count: 16
• Complexity: 212

Purity/Quality:

99% ^*data from raw suppliers

L-Proline benzyl ester hydrochloride 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/38-36/37/38-22
• Safety Statements: 22-24/25-37/39-26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC([NH2+]C1)C(=O)OCC2=CC=CC=C2.[Cl-]
• Isomeric SMILES: C1C[C@H]([NH2+]C1)C(=O)OCC2=CC=CC=C2.[Cl-]
• General Description: L-Proline benzyl ester hydrochloride serves as an effective chiral auxiliary in Lewis acid-catalyzed asymmetric Diels-Alder reactions, enabling high diastereoselectivity and yield in cyclo-adduct formation. Its utility is further enhanced by the ability to recover and reuse the auxiliary from the reaction products, making the process economically viable. Additionally, the proline moiety can be removed through acid-catalyzed hydrolysis of the benzyl ester function, facilitating downstream transformations.

Technology Process of CID 11806790

There total 5 articles about CID 11806790 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: 100.0%

Boc-L-proline benzyl ester (37787-77-2) → benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2020.127676

Reference yield: 93.0%

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) + benzyl alcohol (100-51-6,185532-71-2) → benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4)

Guidance literature:

benzyl alcohol; With thionyl chloride; at 0 ℃; Inert atmosphere;

L-proline; at 0 - 20 ℃; for 50h; Inert atmosphere;

DOI:10.1016/j.bmc.2015.04.061

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4)

Guidance literature:

With diethyl ether;

DOI:10.1021/ja01530a063

upstream raw materials:

L-proline

benzyl alcohol

Boc-L-proline benzyl ester

1-(tert-butoxycarbonyl)-L-proline

Downstream raw materials:

1-[N-(N-benzyloxycarbonyl-L-valyl)-L-tyrosyl]-L-proline-benzyl ester

1-methoxycarbonylmethyl-L-proline-benzyl ester

(S)-1-phenylacetyl-pyrrolidine-2-carboxylic acid benzyl ester

N-(tert-butyloxycarbonyl)-prolyl-proline benzyl ester

Refernces

(S)-Proline Benzyl Ester as Chiral Auxiliary in Lewis Acid Catalyzed Assymetric Diels-Alder Reactions

10.1021/jo00261a034

The research focuses on the application of (S)-proline benzyl ester as a chiral auxiliary in Lewis acid catalyzed asymmetric Diels-Alder reactions. The purpose of this study was to achieve high yields and excellent diastereoselectivities in the formation of cyclo-adducts. The researchers concluded that by using (S)-proline benzyl ester, they could obtain high diastereoselectivities, and the auxiliary could be effectively removed and recovered from the Diels-Alder adducts, making the process economically interesting. The study also involved the transformation of the amide 4a to the ester 5 by O-alkylation with trimethyloxonium tetrafluoroborate and subsequent hydrolysis, as well as the acid-catalyzed hydrolysis of the double bond and benzyl ester function to remove the proline moiety.