(2R,4R)-1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (2R,4R)-1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate
• CAS No.: 155075-23-3
• Molecular Formula: C14H17NO5
• Molecular Weight: 279.293
• DSSTox Substance ID: DTXSID80350898
• Mol file: 155075-23-3.mol

Synonyms:155075-23-3;(2R,4R)-1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate;1-benzyl 2-methyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate;N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER;1-O-benzyl 2-O-methyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate;MFCD09954933;SCHEMBL115971;DTXSID80350898;AMY34582;AKOS015919764;HY-W060779;1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 2-methyl 1-(phenylmethyl) ester, (2R,4R)-;DS-17661;CS-0052633;EN300-7191832;1-benzyl2-methyl(2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate;O1-Benzyl O2-methyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

Chemical Property of (2R,4R)-1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Chemical Property:

• Boiling Point: 422.8±45.0 °C(Predicted)
• PKA: 14.25±0.40(Predicted)
• PSA: 76.07000
• Density: 1.313±0.06 g/cm3(Predicted)
• LogP: 0.86930
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 279.11067264
• Heavy Atom Count: 20
• Complexity: 354

Purity/Quality:

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

N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC(CN1C(=O)OCC2=CC=CC=C2)O
• Isomeric SMILES: COC(=O)[C@H]1C[C@H](CN1C(=O)OCC2=CC=CC=C2)O

Technology Process of (2R,4R)-1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

There total 17 articles about (2R,4R)-1-Benzyl 2-methyl 4-hydroxypyrrolidine-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%

cis-hydroxy-D-proline (2584-71-6,30724-02-8) → (2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (155075-23-3)

Guidance literature:

With sodium hydrogencarbonate; In water; toluene; at 23 ℃; for 24.25h;

Reference yield: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (R,R)-4-hydroxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid (130930-25-5) → (2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (155075-23-3)

Guidance literature:

In diethyl ether; at 0 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2008.11.035

Reference yield: 100.0%

(R,R)-4-hydroxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid (130930-25-5) + diazomethyl-trimethyl-silane (18107-18-1) → (2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (155075-23-3)

Guidance literature:

In methanol;

DOI:10.1016/j.bmcl.2013.06.030

upstream raw materials:

benzyl chloroformate

(2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride

diazomethane

(R,R)-4-hydroxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid

Downstream raw materials:

(2R,4S)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

C₂₁H₂₀N₂O₈

(2R,4R)-benzyl 4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

(2R,4R)-benzyl 4-(tert-butyldimethylsilyloxy)-2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate

Refernces

• 1、 -. "DIHYDROPYRIMIDINE COMPOUNDS AND USES THEREOF IN MEDICINE". Paragraph 00169; 00194. . Retrieved 2019/05/10.
• 2、 -. "COMPOUNDS". Page/Page column 120. . Retrieved 2016/02/12.