(S)-1-Benzyl 2-methyl pyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (S)-1-Benzyl 2-methyl pyrrolidine-1,2-dicarboxylate
• CAS No.: 5211-23-4
• Molecular Formula: C14H17NO4
• Molecular Weight: 263.293
• Hs Code.: 2933990090
• European Community (EC) Number: 803-758-8
• DSSTox Substance ID: DTXSID70350807
• Nikkaji Number: J275.608K
• Wikidata: Q63392133
• Mol file: 5211-23-4.mol

Synonyms:5211-23-4;(S)-1-Benzyl 2-methyl pyrrolidine-1,2-dicarboxylate;N-Z-L-proline methyl ester;S-1-CBZ-Pyrrolidine-2-carboxylic acid Methyl Ester;N-CARBOBENZYLOXY-L-PROLINE METHYL ESTER;1-O-benzyl 2-O-methyl (2S)-pyrrolidine-1,2-dicarboxylate;MFCD00134246;N-Cbz-Pro-OMe;CBZ-L-proline, methyl ester;1-Cbz-L-proline methyl ester;SCHEMBL4724457;DTXSID70350807;1,2-Pyrrolidinedicarboxylic acid, 2-methyl 1-(phenylmethyl) ester, (S)-;Methyl (S)-N-(benzyloxycarbonyl)prolinate;N-Z-L-proline methyl ester, 97%;AKOS015851014;AKOS015898050;N-benzyloxycarbonylproline methyl ester;DS-6654;benzyl-oxycarbonyl-l-proline methyl ester;HY-41318;CS-0015967;N-(Benzyloxycarbonyl)-L-proline methyl ester;N-benzyloxycarbonyl-(S)-proline methyl ester;A871066;(5)-1-benzyl 2-methyl pyrrolidine-1,2-dicarboxylate;(S)-1-cbz-pyrrolidine-2-carboxylic acid methyl ester;N-(BENZYLOXYCARBONYL)-(S)-PROLINE METHYL ESTER;Q63392133;1-Benzyl 2-methyl (2S)-pyrrolidine-1,2-dicarboxylate

Chemical Property of (S)-1-Benzyl 2-methyl pyrrolidine-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 8.02E-06mmHg at 25°C
• Refractive Index: n20/D 1.5217(lit.)
• Boiling Point: 375°C at 760 mmHg
• PKA: -3.40±0.40(Predicted)
• Flash Point: >230 °F
• PSA: 55.84000
• Density: 1.175 g/mL at 25 °C(lit.)
• LogP: 1.89850
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 263.11575802
• Heavy Atom Count: 19
• Complexity: 325

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Z-L-proline methyl ester 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCCN1C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: COC(=O)[C@@H]1CCCN1C(=O)OCC2=CC=CC=C2

Technology Process of (S)-1-Benzyl 2-methyl pyrrolidine-1,2-dicarboxylate

There total 38 articles about (S)-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: 100.0%

methanol (67-56-1) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → N-carbobenzyloxy-L-proline methyl ester (5211-23-4)

Guidance literature:

With thionyl chloride; rt., 1 h, then reflux, 2 h;

DOI:10.1002/hlca.19970800514

Reference yield: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → N-carbobenzyloxy-L-proline methyl ester (5211-23-4)

Guidance literature:

In diethyl ether;

DOI:10.1039/b822944a

Reference yield: 94.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + N-Cbz-Prolinol (6216-63-3) → N-carbobenzyloxy-L-proline methyl ester (5211-23-4)

Guidance literature:

N-Cbz-Prolinol; With sodium chlorite; sodium dihydrogenphosphate; Me-AZADO+Cl-; In dichloromethane; water; at 25 ℃; for 15h;

With 2-methyl-but-2-ene; In dichloromethane; water;

diazomethane; With hydrogenchloride; sodium hydroxide; more than 3 stages; Product distribution / selectivity;

upstream raw materials:

methanol

(S)-benzyloxycarbonyl-proline acid chloride

O-benzyl 2,2,2-trichloroacetimidate

(S)-N-(tert-butoxycarbonyl)proline methyl ester

Downstream raw materials:

(S)-diphenylprolinol

(5S)-2-Methoxy-1-[(benzyloxy)carbonyl]-5-methoxycarbonylpyrrolidine

(2S)-N-Benzyloxycarbony-2-(1'-hydroxy-1'-methylethyl)pyrrolidine

benzyl (S)-(-)-2-(hydroxy(diphenyl)methyl)-1-pyrrolidine carboxylate

Refernces

• 1、 Katakam, Nanda Kumar,Seifert, Cole W.,D'Auria, John,Li, Guigen. "Efficient synthesis of methyl (S)-4-(1-methylpyrrolidin-2-YL)-3-oxobutanoate as the key intermediate for tropane alkaloid biosynthesis with optically acitve form". . p. 604 - 613. Retrieved 2019/08/01.
• 2、 Br?uer, Thomas M.,Zhang, Qi,Tiefenbacher, Konrad. "Iminium Catalysis inside a Self-Assembled Supramolecular Capsule: Modulation of Enantiomeric Excess". supporting information. p. 7698 - 7701. Retrieved 2016/07/07.