1-BENZYL 2-METHYL PYRROLIDINE-1,2-DICARBOXYLATE

Base Information

• Chemical Name: 1-BENZYL 2-METHYL PYRROLIDINE-1,2-DICARBOXYLATE
• CAS No.: 108645-62-1
• Molecular Formula: C14H17NO4
• Molecular Weight: 263.293
• Hs Code.: 2933990090
• Mol file: 108645-62-1.mol

Synonyms:LABOTEST-BB LT00453234;1-BENZYL 2-METHYL PYRROLIDINE-1,2-DICARBOXYLATE;PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-BENZYL ESTER 2-METHYL ESTER;1,2-Pyrrolidinedicarboxylic acid, 2-Methyl 1-(phenylMethyl) ester

Chemical Property of 1-BENZYL 2-METHYL PYRROLIDINE-1,2-DICARBOXYLATE

Chemical Property:

• Boiling Point: 375.0±42.0 °C(Predicted)
• PKA: -3.40±0.40(Predicted)
• PSA: 55.84000
• Density: 1.220±0.06 g/cm3(Predicted)
• LogP: 1.89850
• Storage Temp.: 2-8°C

Purity/Quality:

99.3% ^*data from raw suppliers

1-Benzyl2-methylpyrrolidine-1,2-dicarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-BENZYL 2-METHYL PYRROLIDINE-1,2-DICARBOXYLATE

There total 17 articles about 1-BENZYL 2-METHYL PYRROLIDINE-1,2-DICARBOXYLATE 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: 98.0%

N-carbobenzyloxyproline (1148-11-4) + methyl iodide (74-88-4) → N-benzyloxycarbonylproline methyl ester (108645-62-1)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0957-4166(03)00210-6

Reference yield: 81.0%

methanol (67-56-1) + N-carbobenzyloxyproline (1148-11-4) → N-benzyloxycarbonylproline methyl ester (108645-62-1)

Guidance literature:

With sulfuric acid; for 3h; Reflux;

DOI:10.1016/j.tet.2012.12.004

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → N-benzyloxycarbonylproline methyl ester (108645-62-1)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaHCO₃ / tetrahydrofuran / 6 h / 20 °C

2: diethyl ether / 0.17 h / 20 °C

With sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether;

DOI:10.1002/anie.200601506

upstream raw materials:

sodium methylate

S-(3-mercaptopropyl) N-benzyloxycarbonylpyrrolidine-2-carbothioate

methanol

N-carbobenzyloxyproline

Downstream raw materials:

1-Benzyloxycarbonyl-2-(methoxycarbonyl)-2-(2-propenyl)pyrrolidine

2-iodomethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

(S)-2-formyl-1-pyrrolidinecarboxylic acid,phenylmethyl ester

(RS)-2-allyl-N-(benzyloxycarbonyl)proline

Refernces

• 1、 Hayashi, Yujiro,Matsuzawa, Masayoshi,Yamaguchi, Junichiro,Yonehara, Sayaka,Matsumoto, Yasunobu,Shoji, Mitsuru,Hashizume, Daisuke,Koshino, Hiroyuki. "Large nonlinear effect observed in the enantiomeric excess of proline in solution and that in the solid state". . p. 4593 - 4597. Retrieved 2006.
• 2、 Loughlin, Wendy A.,Schweiker, Stephanie S.,Jenkins, Ian D.,Henderson, Luke C.. "Synthesis and evaluation of C8-substituted 4.5-spiro lactams as Glycogen Phosphorylase a inhibitors". supporting information. p. 1576 - 1582. Retrieved 2013/03/29.
• 3、 Kurokawa, Masayuki,Shindo, Takeyuki,Suzuki, Masumi,Nakajima, Nobuyoshi,Ishihara, Kohji,Sugai, Takeshi. "Enzyme-catalyzed enantiomeric resolution of N-Boc-proline as the key-step in an expeditious route towards RAMP". . p. 1323 - 1333. Retrieved 2007/10/03.