Tert-butyl pyrrolidine-2-carboxylate

Base Information

• Chemical Name: Tert-butyl pyrrolidine-2-carboxylate
• CAS No.: 2812-46-6
• Molecular Formula: C9H17NO2
• Molecular Weight: 171.239
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40950858
• Nikkaji Number: J1.154.287E
• Mol file: 2812-46-6.mol

Synonyms:tert-butyl pyrrolidine-2-carboxylate;113131-45-6;tert-butyl prolinate;MFCD00083683;pyrrolidine-2-carboxylic acid tert-butyl ester;Proline1,1-diMethylethylester;SCHEMBL248746;DTXSID40950858;XJJBXZIKXFOMLP-UHFFFAOYSA-N;tert-butylpyrrolidine-2-carboxylate;EINECS 220-558-0;AKOS010135091;AC-19232;DS-13953;SY239795;2-pyrrolidinecarboxylic acid tert-butyl ester;CS-0441253;FT-0659096;FT-0699179;C77766;EN300-147771;A819336

Chemical Property of Tert-butyl pyrrolidine-2-carboxylate

Chemical Property:

• Appearance/Colour: Oil
• Vapor Pressure: 0.121mmHg at 25°C
• Melting Point: 98-103°C
• Refractive Index: 1.454
• Boiling Point: 219.2 °C at 760 mmHg
• PKA: 8.32±0.10(Predicted)
• Flash Point: 86.4 °C
• PSA: 38.33000
• Density: 0.995 g/cm³
• LogP: 1.40890
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 171.125928785
• Heavy Atom Count: 12
• Complexity: 172

Purity/Quality:

99% ^*data from raw suppliers

L-Proline tert-butyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1CCCN1
• Uses: L-Proline tert-Butyl Ester is a tert-Butyl ester of L-Proline (P755995) which is an amino acid and precursor (with vitamin C) for collagen, the building block of the structure of tendons, ligaments, arteries, veins and muscles. It is important in wound healing.

Technology Process of Tert-butyl pyrrolidine-2-carboxylate

There total 23 articles about Tert-butyl pyrrolidine-2-carboxylate 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%

(S)-2-tert-butyl-1-benzylpyrrolidine-1,2-dicarboxylate (16881-39-3) → proline tert-butyl ester (2812-46-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 5h;

DOI:10.1039/c6ob01783e

Reference yield: 88.0%

N-BOC-proline tert-butyl ester (91237-84-2) → proline tert-butyl ester (2812-46-6)

Guidance literature:

With tin(II) trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1081/SCC-120015775

Reference yield: 83.0%

(S)-2-Amino-5-hydroxy-pentanoic acid tert-butyl ester → proline tert-butyl ester (2812-46-6)

Guidance literature:

With 1H-imidazole; bromine; triphenylphosphine; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1002/ejoc.200400370

upstream raw materials:

(S)-2-tert-butyl-1-benzylpyrrolidine-1,2-dicarboxylate

2-tert-butyl-1,3-diisopropylisourea

L-proline

(9H-fluoren-9-yl)methyl tert-butylpyrrolidine-1,2-dicarboxylate

Downstream raw materials:

N-Benzyloxycarbonyl-γ-(S)-glutamyl(α-tert.-butylester)-(S)-prolin-tert.-butylester

Z₃-Arg-Pro-t-Bu

N-Fmoc-Phe-Pro-OBu^t

(R)-1-[(2S,3S)-3-Methyl-2-(2-nitro-benzenesulfonylamino)-pentanoyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

Refernces

• 1、 Minkovich, Boris,Ruderfer, Ilya,Kaushansky, Alexander,Bravo-Zhivotovskii, Dmitry,Apeloig, Yitzhak. "α-Sila-Dipeptides: Synthesis and Characterization". . p. 13261 - 13265. Retrieved 2018.
• 2、 Albat, Dominik,Neud?rfl, J?rg-Martin,Schmalz, Hans-Günther. "A General Stereocontrolled Synthesis of Opines through Asymmetric Pd-Catalyzed N-Allylation of Amino Acid Esters". supporting information. p. 2099 - 2102. Retrieved 2021/07/22.