174060-99-2

Basic information

• Product Name: (2S,4S)-N-Boc-4-hydroxy-3,3-dimethylpyrrolidine-2-carboxylic acid
• Synonyms: (2s,4s)-n-boc-4-hydroxy-3,3-dimethylpyrrolidine-2-carboxylic acid;(2S,4S)-1-(tert-Butoxycarbonyl)-4-hydroxy-3,3-dimethylpyrrolidine-2-carboxylic acid;(2S,4S)-4-Hydroxy-3,3-dimethyl-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) ester
• CAS NO: 174060-99-2
• Molecular Formula: C₁₂H₂₁NO₅
• Molecular Weight: 259.3
• Mol File: 174060-99-2.mol

Chemical Properties

• Boiling Point: 392.123 °C at 760 mmHg
• Flash Point: 190.95 °C
• Appearance: /
• Density: 1.208
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.507
• PKA: 3.83±0.60(Predicted)
• CAS DataBase Reference: (2S,4S)-N-Boc-4-hydroxy-3,3-dimethylpyrrolidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-N-Boc-4-hydroxy-3,3-dimethylpyrrolidine-2-carboxylic acid(174060-99-2)
• EPA Substance Registry System: (2S,4S)-N-Boc-4-hydroxy-3,3-dimethylpyrrolidine-2-carboxylic acid(174060-99-2)

Safety Data

• Hazardous Substances Data: 174060-99-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(2S,4S)-N-Boc-4-hydroxy-3,3-dimethylpyrrolidine-2-carboxylic acid serves as a key building block in the synthesis of pharmaceuticals, leveraging its functional groups to form crucial amide and ester bonds in drug molecules.
Used in Biologically Active Compounds Synthesis:
(2S,4S)-N-Boc-4-hydroxy-3,3-dimethylpyrrolidine-2-carboxylic acid is also utilized in the synthesis of biologically active compounds, where its chiral centers and functional groups contribute to the development of molecules with specific biological activities.
Used in Enantioselective Catalysts Development:
(2S,4S)-N-Boc-4-hydroxy-3,3-dimethylpyrrolidine-2-carboxylic acid is employed in the creation of enantioselective catalysts, capitalizing on its chiral nature to achieve high selectivity in asymmetric reactions.
Used in Chiral Ligands Synthesis:
It is used as a precursor in the synthesis of chiral ligands, which are essential for asymmetric catalysis and enantioselective synthesis, enhancing the efficiency and selectivity of chemical reactions.
Used in Research and Development:
In the research and development industry, (2S,4S)-N-Boc-4-hydroxy-3,3-dimethylpyrrolidine-2-carboxylic acid is used for studying the effects of stereochemistry on the properties and reactivity of molecules, contributing to the advancement of organic chemistry and drug discovery.

InChI:InChI=1/C12H21NO5/c1-11(2,3)18-10(17)13-6-7(14)12(4,5)8(13)9(15)16/h7-8,14H,6H2,1-5H3,(H,15,16)/t7-,8-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 173913-63-8 (2S)-3,3-dimethyl-4-oxo-N-(9-phenylfluoren-9-yl)proline benzyl ester 
• 173913-65-0 (2S,4S)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester 
• 593-51-1 methylamine hydrochloride 

Relevant articles and documents

HIV PROTEASE INHIBITORS, COMPOSITIONS CONTAINING THE SAME AND THEIR PHARMACEUTICAL USES

This invention relates to a novel series of chemical compounds useful as Human immunodeficiency Virus (HIV) protease inhibitors and to the use of such compounds as antiviral agents. The invention further relates to pharmaceutical compositions containing s

Regioselective enolization and alkylation of 4-oxo-N-(9-phenylfluoren-9-yl)proline: Synthesis of enantiopure proline-valine and hydroxyproline-valine chimeras

The regioselective enolization of 4-oxo-N-(9-phenylfluoren-9-yl)proline benzyl ester (5) followed by alkylation with different alkyl halides has been used to synthesize a variety of β-alkylproline derivatives. In particular, enolization of 5 with 400 mol % of KN(SiMe3)2 and alkylation with iodomethane provided 3,3-dimethyl-4-oxo-N-(9-phenylfluoren-9-yl)proline benzyl ester (7a) in excellent yield. Subsequent hydride reduction of ketone 7a and protecting group exchange by hydrogenation in the presence of di-tert-butyl dicarbonate provided enantiopure (2S,4R)- and (2S,-4S)-3,3-dimethyl-4-hydroxy-N-(BOC)prolines 2. Hydroxyproline-valine chimeras (2S,4R)- and (2S,4S)-2 are each synthesized from hydroxyproline in six steps and 27% respective overall yield. Deoxygenation of 3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl esters 9 via their conversion to xanthates 10 followed by tributylstannane-mediated reduction provided 3,3-dimethyl-N-(9-phenylfluoren-9-yl)proline benzyl ester (11) in excellent yield. Hydrogenation of 11 with Pearlman's catalyst in the presence of di-tert-butyl dicarbonate then furnished (2S)-3,3-dimethyl-N-(BOC)proline (1) in the last step of an eight-step synthesis (41% overall yield) from hydroxyproline. Both proline-valine and hydroxyproline-valine chimeras 1 and 2 were designed to serve as tools for studying the conformational requirements of biologically active peptides.