185142-15-8

Basic information

• Product Name: (2S,5R)-N-Boc-5-tert-butylpyrrolidine-2-carboxylic acid
• Synonyms: (2s,5r)-n-boc-5-tert-butylpyrrolidine-2-carboxylic acid;(2S,5R)-1-(tert-Butoxycarbonyl)-5-tert-butylpyrrolidine-2-carboxylic acid;(2S,5R)-5-(1,1-Dimethylethyl)-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) ester;(2s,5r)-n-boc-5-tert-butylpyrrolidine-2-carboxylic acid:(2s,5r)-1-(tert-butoxycarbonyl)-5-tert-butylpyrrolidine-2-carboxylic acid
• CAS NO: 185142-15-8
• Molecular Formula: C₁₄H₂₅NO₄
• Molecular Weight: 271.35
• Mol File: 185142-15-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 373.8 °C at 760 mmHg
• Flash Point: 179.9 °C
• Appearance: /
• Density: 1.105
• Refractive Index: 1.491
• PKA: 4.02±0.40(Predicted)
• CAS DataBase Reference: (2S,5R)-N-Boc-5-tert-butylpyrrolidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R)-N-Boc-5-tert-butylpyrrolidine-2-carboxylic acid(185142-15-8)
• EPA Substance Registry System: (2S,5R)-N-Boc-5-tert-butylpyrrolidine-2-carboxylic acid(185142-15-8)

Safety Data

• Hazardous Substances Data: 185142-15-8(Hazardous Substances Data)

Usage

General Description

The chemical compound (2S,5R)-N-Boc-5-tert-butylpyrrolidine-2-carboxylic acid is a derivative of pyrrolidine, containing a tert-butyl group and a carboxylic acid functional group. It is chiral, with a stereochemistry of 2S,5R. The Boc group is a protective group for the amine, which can be removed under specific conditions. (2S,5R)-N-Boc-5-tert-butylpyrrolidine-2-carboxylic acid may have applications in organic synthesis and medicinal chemistry, as pyrrolidine derivatives are commonly used as building blocks in the synthesis of pharmaceuticals and biologically active compounds. Its specific properties and potential uses would depend on further study and research.

InChI:InChI=1/C14H25NO4/c1-13(2,3)10-8-7-9(11(16)17)15(10)12(18)19-14(4,5)6/h9-10H,7-8H2,1-6H3,(H,16,17)/t9-,10+/m0/s1

Upstream product

• 185142-08-9 methyl 6,6-dimethyl-5-oxo-2-[N-(9-(9-phenylfluorenyl))amino]heptanoate 
• 185142-06-7 (S)-6,6-Dimethyl-5-oxo-2-(9-phenyl-9H-fluoren-9-ylamino)-heptanoic acid 
• 3282-30-2 pivaloyl chloride 
• 653605-46-0 (S)-2-(2,2-Dimethyl-propionyl)-4-(trityl-amino)-pentanedioic acid 1-methyl ester 
• 185064-53-3 methyl (2S,5R)-(-)-N-(tert-butyloxycarbonyl)-5-(tert-butylpyrrolidine)-2-carboxylate 
• 185142-04-5 (2S,4RS)-6,6-dimethyl-5-oxo-4-<(methyloxy)carbonyl>-2-heptanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 224951-63-7 N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline allyl ester 
• 224951-72-8 N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline N'-methylamide 
• 412303-26-5 N-(tert-butoxycarbonyl)-(S)-phenylalanyl-(2S,5R)-5-tert-butylproline benzyl ester 
• 412303-25-4 N-(tert-butoxycarbonyl)-(S)-leucyl-(2S,5R)-5-tert-butylproline benzyl ester 
• 412303-24-3 N-(tert-butoxycarbonyl)-(S)-alanyl-(2S,5R)-5-tert-butylproline benzyl ester 
• 224951-66-0 N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline 

Relevant articles and documents

COMPOUNDS HAVING PROLYL OLIGOPEPTIDASE INHIBITORY ACTIVITY

The invention provides a compound of formula (I), wherein in the formula X, R1, R2 and R3 are as defined in claim 1, or a pharmaceutically acceptable salt or ester thereof, useful as a prolyl oligopeptidase inhibitor. The compounds of formula (I) can be used for the treatment of diseases or conditions where prolyl oligopeptidase inhibitors are indicated to be effective, for example for the treatment of neurodegenerative diseases, such as Alzheimer's disease and senile dementia

5-tert-butylproline

Steric effects on the isomer equilibrium of amides N-terminal to proline can be explored with 5-alkylprolines having bulky 5-position substituents. Enantiopure 5-tert-butylprolines were thus synthesized from glutamic acid via an acylation/diastereoselective reductive amination sequence. Double deprotonation of γ-methyl N-(PhF)glutamate (2) with LiN(SiMe3)2 and C-acylation with pivaloyl chloride provided β-keto ester 3, which upon γ-ester hydrolysis and decarboxylation gave δ-oxo-α-[N-(PhF)amino]heptanoic acid (4). Syntheses of (2S,5R)- and (2R,5S)-N-(BOC)-5-tert-butylprolines ((2S,5R)-1 and (2R,5S)-1) were accomplished by catalytic hydrogenation of their respective (2S)- and (2R)-methyl δ-oxo-α-[N-(PhF)amino]heptanoates ((2S)-5a and (2R)-5a) in methanol with di-tert-butyl dicarbonate followed by chromatography and ester hydrolysis with potassium trimethylsilanolate. The 5-tert-butylproline cis-diastereomers were proven to be of >99% enantiomeric purity after their conversion to diastereomeric α-methylbenzylamides 10. Good diastereoselectivity in favor of the trans-diastereomer was observed when (2S,5S)-5-tert-butylproline was synthesized from (2S)-δ-oxo-α-[N-(PhF)amino]heptanoate ((2S)-4) by solvolysis of the PhF group in trifluoroacetic acid and subsequent reduction of 5-tert-butyl-Δ5-dehydroproline (11) with tetramethylammonium triacetoxyborohydride; however, imino acid 11 was shown to be configurationally labile and racemized under acidic conditions. 5-tert-Butyl-Δ5-dehydroproline N'-methylamide 15 was configurationally stable in acid, yet preliminary attempts to reduce 15 favored cis-diastereomer 16. Alternatively, enantiopure trans-diastereomer, (2R,5R)-methyl N-(BOC)-5-tert-butylprolinate (9) was prepared by epimerization of (2S,5R)-9. In summary, this synthetic methodology now provides access to all four enantiopure 5-tert-butylproline isomers from inexpensive L- and D-glutamate as chiral educts.