(2R,5S)-BOC-5-PHENYL-PYRROLIDINE-2-CARBOXYLIC ACID

Base Information

• Chemical Name: (2R,5S)-BOC-5-PHENYL-PYRROLIDINE-2-CARBOXYLIC ACID
• CAS No.: 158706-46-8
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347
• Hs Code.: 29339900
• Mol file: 158706-46-8.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, 5-phenyl-, 1,1-dimethylethyl ester, (2R-cis)-;(2R,5S)-1-Boc-5-phenylpyrrolidine-2-carboxylic acid;(2R,5S)-5-Phenylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Chemical Property of (2R,5S)-BOC-5-PHENYL-PYRROLIDINE-2-CARBOXYLIC ACID

Chemical Property:

• Boiling Point: 441.5±45.0 °C(Predicted)
• PKA: 3.90±0.40(Predicted)
• PSA: 66.84000
• Density: 1.196±0.06 g/cm3(Predicted)
• LogP: 3.14970
• Storage Temp.: Store at -15°C

Purity/Quality:

95-99% ^*data from raw suppliers

Boc-(2R,5S)-5-phenyl-pyrrolidine-2-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,5S)-BOC-5-PHENYL-PYRROLIDINE-2-CARBOXYLIC ACID

There total 13 articles about (2R,5S)-BOC-5-PHENYL-PYRROLIDINE-2-CARBOXYLIC ACID 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: 49.0%

1.0 M-NaOH + benzyl 5-phenyl-5-pyrroline-(2S)-carboxylate + di-tert-butyl dicarbonate (24424-99-5) → (2S,5R)-(tert-butyloxycarbonyl)-5-phenylpyrrolidine-2-carboxylic acid (221352-49-4,158706-46-8)

Guidance literature:

palladium-carbon; In methanol; CH₃CN-H₂O;

Reference yield:

(2RS,5R)-2-cyano-5-phenylpyrrolidine-1-carboxylic acid t-butyl ester (663956-49-8) → (2RS,5R)-1-(t-butoxycarbonyl)-5-phenylpyrrolidine-2-carboxylic acid (663956-50-1,158706-46-8)

Guidance literature:

With sodium hydroxide; water; In methanol; at 20 - 75 ℃; for 6h;

Reference yield:

(2S/R,5R/S)-1-tert-butyl 2-methyl 5-phenylpyrrolidine-1,2-dicarboxylate → (2S/R,5R/S)-1-(tert-butoxycarbonyl)-5-phenylpyrrolidine-2-carboxylic acid (158706-46-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 16h;

upstream raw materials:

di-tert-butyl dicarbonate

rac-1-(tert-butyl) 2-methyl 5-oxopyrrolidine-1,2-dicarboxylate

phenylmagnesium bromide

(2RS,5R)-2-cyano-5-phenylpyrrolidine-1-carboxylic acid t-butyl ester

Downstream raw materials:

(2S,5R)-2-(methylaminomethyl)-1-methyl-5-phenylpyrrolidine

Refernces

• 1、 Claraz, Aurlie,Sahoo, Gokarneswar,Berta, Dnes,Madarsz, dm,Ppai, Imre,Pihko, Petri M.. "A Catalyst Designed for the Enantioselective Construction of Methyl- and Alkyl-Substituted Tertiary Stereocenters". . p. 669 - 673. Retrieved 2016/02/27.
• 2、 -. "NITROGEN-CONTAINING COMPOUNDS". Page/Page column 37. . Retrieved 2010/02/11.