123724-32-3

Usage

Uses

Used in Organic Synthesis:
(2R,3S)-1-(tert-butoxycarbonyl)-3-phenylpyrrolidine-2-carboxylic acid is used as a protected intermediate in organic synthesis for the preparation of various pharmaceuticals and bioactive compounds. The Boc protecting group allows chemists to carry out reactions selectively at other sites on the molecule, facilitating the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In pharmaceutical research, (2R,3S)-1-(tert-butoxycarbonyl)-3-phenylpyrrolidine-2-carboxylic acid serves as a key intermediate for the development of new drugs. Its unique stereochemistry and functional groups can be exploited to design molecules with specific biological activities, potentially leading to the discovery of novel therapeutic agents.
Used in the Production of Other Compounds:
(2R,3S)-1-(tert-butoxycarbonyl)-3-phenylpyrrolidine-2-carboxylic acid is also utilized as a precursor in the synthesis of other complex organic compounds. Its versatility and the presence of the Boc protecting group make it an attractive candidate for the production of specialty chemicals and materials with tailored properties for various applications.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 123724-30-1 (2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide 
• 118758-50-2 trans-3-phenyl-(R)-proline 
• 246232-25-7 (2R,3S)-β-phenyl-pyroglutamic acid 
• 246231-99-2 ethyl (2R,3S)-3-phenylpyroglutamate 
• 123807-03-4 N-acetyl-trans-3-phenylproline 
• 1187592-04-6 C₁₆H₂₁NO₃ 
• 3005-63-8 1-acetyl-5-hydroxy-3-phenyl-pyrrolidine-2,2-dicarboxylic acid diethyl ester 
• 14371-10-9 (E)-3-phenylpropenal 
• 1426559-88-7 methyl (2R,3S)-N-(tert-butoxycarbonyl)-β-phenylprolinate 
• 210420-48-7 (2RS,3SR)-N-(tert-butoxycarbonyl)-β-phenylproline 
• 143979-44-6 1-(tert-butoxycarbonyl)-3-phenylproline 
• 1426559-89-8 C₁₁H₁₃NO₂*ClH 
• 179601-45-7 N-acetyl-3-phenylproline ethyl ester 

Relevant academic research and scientific papers

Access to enantiomerically pure cis- and trans-β-phenylproline by high-performance liquid chromatography resolution

The preparation of all four stereoisomers of the proline analog that bears a phenyl group attached to the β carbon either cis or trans to the carboxylic acid (cis- and trans-β-phenylproline, respectively) has been addressed. The methodology developed allows access to multigram quantities of the target amino acids in enantiomerically pure form and suitably protected for use in peptide synthesis. Racemic precursors of cis-β-phenylproline and trans-β-phenylproline were prepared from easily available starting materials and subjected to high-performance liquid chromatography enantioseparation. Semipreparative columns (250 × 20 mm) containing chiral stationary phases based on amylose (Chiralpak IA) (Daicel-Chiral Technologies Europe, Illkirch, France) or cellulose (Chiralpak IC) were used respectively for the resolution of the cis- and trans-β-phenylproline precursors. Chirality, 24:1082-1091, 2012. 2012 Wiley Periodicals, Inc. Copyright

Diphenylprolinol silyl ether as a catalyst in an asymmetric, catalytic, and direct michael reaction of nitroethanol with α,β-unsaturated aldehydes

Diphenylprollnol silyl ether was found to be an effective organocatalyst in the enantioselective and direct Michael reaction of nitroethanol and α,β-unsaturated aldehydes, affording the 1-hydroxy-trans-3,4- disubstituted tetrahydropyrans after isomerizatl

Organocatalytic asymmetric 5-hydroxypyrrolidine synthesis: a highly enantioselective route to 3-substituted proline derivatives

The highly enantioselective organocatalytic tandem reaction between 2-acylaminomalonates and α,β-unsaturated aldehydes is presented. The reaction is a direct entry to 5-hydroxypyrrolidines and 3-substituted proline derivatives, which are furnished in high

Virtually complete control of simple and face diastereoselectivity in the Michael addition reactions between achiral equivalents of a nucleophilic glycine and (S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones: Practical method for preparation of β-substituted pyroglutamic acids and prolines

This study demonstrates a new strategy for controlling the stereochemical outcome of the Michael addition reactions between nucleophilic glycine equivalents and α,β-unsaturated carboxylic acid derivatives: The addition reactions between achiral Ni(II)-complex of the Schiff base of glycine with o-[N-α-pycolylamino]acetophenone and (S)- or (R)-3-(E-enoyl)-4- phenyl-1,3-oxazolidin-2-ones were shown to occur at room temperature in the presence of nonchelating organic bases and, most notably, with very high stereoselectivity at both newly formed stereogenic centers. Thus, the chiral 4-phenyl-1,3-oxazolidin-2-one moiety was found to control efficiently both face diastereoselectivities of the glycine derived enolate and the C,C double bond of the Michael acceptor. The new strategy developed in this work is methodologically superior to previous methods, most notably in terms of generality and synthetic efficiency. Excellent chemical yields and diastereoselectivities, combined with the simplicity of the experimental procedures, render the present method of immediate use for preparing various 3-substituted pyroglutamic acids and related amino acids (glutamic acids, glutamines, prolines, etc.) available via conventional transformations of the former.

A convenient synthetic route to macrocyclic cis-3-phenylproline derivatives as mimics of Sandostatin

Enantiomerically pure 14- and 20-membered cyclic proline derivatives 2a- d were conveniently prepared from cis-3-phenylproline using macrolactonisation or macrolactamisation reactions.