Methyl (2S,4R)-4-hydroxy-1-(9-phenylfluoren-9-yl)pyrrolidine-2-carboxylate

Base Information

• Chemical Name: Methyl (2S,4R)-4-hydroxy-1-(9-phenylfluoren-9-yl)pyrrolidine-2-carboxylate
• CAS No.: 179990-59-1
• Molecular Formula: C25H23NO3
• Molecular Weight: 385.463
• DSSTox Substance ID: DTXSID30455605
• Nikkaji Number: J2.404.611G
• Wikidata: Q82277687
• Mol file: 179990-59-1.mol

Synonyms:179990-59-1;Methyl (2S,4R)-4-hydroxy-1-(9-phenylfluoren-9-yl)pyrrolidine-2-carboxylate;(4R, 2S)-4-Hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-proline Methyl Ester;L-Proline, 4-hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-, methyl ester, (4R)-;DTXSID30455605;MJIVTEQYUJILHQ-JPYJTQIMSA-N;AKOS030241165;CID 11111807;1-(9-Phenyl-9H-fluorene-9-yl)-4beta-hydroxy-L-proline methyl ester;Methyl (4R)-4-hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-L-prolinate;(2S,4R)-Methyl 4-hydroxy-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate;(2S,4R)-Methyl4-hydroxy-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate

Chemical Property of Methyl (2S,4R)-4-hydroxy-1-(9-phenylfluoren-9-yl)pyrrolidine-2-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 63-66°C°C
• Boiling Point: 520.296oC at 760 mmHg
• Flash Point: 268.466oC
• PSA: 49.77000
• Density: 1.289g/cm3
• LogP: 3.50500
• Storage Temp.: Refrigerator
• Solubility.: Chloroform
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 385.16779360
• Heavy Atom Count: 29
• Complexity: 579

Purity/Quality:

97% ^*data from raw suppliers

(4R,2S)-4-Hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-prolineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC(CN1C2(C3=CC=CC=C3C4=CC=CC=C42)C5=CC=CC=C5)O
• Isomeric SMILES: COC(=O)[C@@H]1C[C@H](CN1C2(C3=CC=CC=C3C4=CC=CC=C42)C5=CC=CC=C5)O
• Uses: (4R, 2S)-4-Hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-proline Methyl Ester (cas# 179990-59-1) is a compound useful in organic synthesis.

Technology Process of Methyl (2S,4R)-4-hydroxy-1-(9-phenylfluoren-9-yl)pyrrolidine-2-carboxylate

There total 4 articles about Methyl (2S,4R)-4-hydroxy-1-(9-phenylfluoren-9-yl)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: 82.0%

9-bromo-9-phenyl-9H-fluorene (55135-66-5) + (R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2) → (2S,4R)-4-hydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester (179990-59-1)

Guidance literature:

With chloro-trimethyl-silane; lead(II) nitrate; In dichloromethane;

DOI:10.1016/S0040-4039(00)74441-8

Reference yield: 68.0%

(2S)-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester (160882-76-8) → methyl (2S,4S)-4-hydroxy-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate (1236783-98-4) + (2S,4R)-4-hydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester (179990-59-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jo1009239

Reference yield:

9-bromo-9-phenyl-9H-fluorene (55135-66-5) + L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4R)-4-hydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester (179990-59-1)

Guidance literature:

With chloro-trimethyl-silane; lead(II) nitrate; triethylamine; Yield given. Multistep reaction; 1) CH₂Cl₂, reflux, 1 h; 2) CH₂Cl₂, MeOH, rt, 96 h;

DOI:10.1021/jo9604245

upstream raw materials:

9-bromo-9-phenyl-9H-fluorene

(R)-4-hydroxy-L-proline ethyl ester

L-4-hydroxyproline methyl ester hydrochloride

4R-4-hydroxyproline

Downstream raw materials:

(2S)-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

(2S,3S,1''R)-3-[1''-phenyl-1''-hydroxymethyl]-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester