178172-26-4

Basic information

• Product Name: (S)-1-Boc-2,3-dihydro-2-pyrrolecarboxylic acid ethyl ester
• Synonyms: (S)-1-Boc-2,3-dihydro-2-pyrrolecarboxylic acid ethyl ester;ethyl N- Boc- 4,5- dehydroprolinate;(S)-1-tert-Butyl 2-ethyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate;Ethyl N-Boc-L-proline-4-ene;Saxagliptin Intermediate 1;1-O-tert-butyl 2-O-ethyl (2S)-2,3-dihydropyrrole-1,2-dicarboxylate
• CAS NO: 178172-26-4
• Molecular Formula: C₁₂H₁₉NO₄
• Molecular Weight: 241.28
• Mol File: 178172-26-4.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 315.631 °C at 760 mmHg
• Flash Point: 144.689 °C
• Appearance: /
• Density: 1.126 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.49
• Storage Temp.: 2-8°C
• PKA: -2.52±0.40(Predicted)
• CAS DataBase Reference: (S)-1-Boc-2,3-dihydro-2-pyrrolecarboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-Boc-2,3-dihydro-2-pyrrolecarboxylic acid ethyl ester(178172-26-4)
• EPA Substance Registry System: (S)-1-Boc-2,3-dihydro-2-pyrrolecarboxylic acid ethyl ester(178172-26-4)

Safety Data

• Hazardous Substances Data: 178172-26-4(Hazardous Substances Data)

Usage

Chemical Properties

pale yelllow oily liquid

InChI:InChI=1/C12H19NO4/c1-5-16-10(14)9-7-6-8-13(9)11(15)17-12(2,3)4/h6,8-9H,5,7H2,1-4H3/t9-/m0/s1

Upstream product

• 98-79-3 L-Pyroglutamic acid 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 194594-24-6 (2S)-1-t-butyl 2-ethyl 5-methoxypyrrolidine-1,2-dicarboxylate 
• 194594-23-5 5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 

Downstream Products

• 709031-43-6 3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.1^3,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester 
• 1564265-93-5 saxagliptin 
• 1564265-93-5 (R)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile 
• 1564265-93-5 (2S,4S,5R)-2-[(2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile 
• 1564265-98-0 (R)-3-hydroxyadamantylglycine-L-trans-4,5-methanoprolinenitrile 
• 361440-67-7 [1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester 
• 709031-45-8 (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid 
• 361442-01-5 tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.1³'⁷]dec-1-yl)-2-oxoethyl]carbamate 
• 214193-10-9 2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester 
• 214193-11-0 (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-formic acid ethyl ester 
• 361440-57-5 C₈H₁₃NO₂ 
• 197142-36-2 (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 
• 361440-69-9 (2S,4S,5S)-4,5-methano-L-proline carboxylamide trifluoroacetate 
• 709031-78-7 Saxagliptin hydrochloride 

Relevant articles and documents

Probing the importance of spacial and conformational domains in captopril analogs for angiotensin converting enzyme activity

A new synthesis of 4,5-methano-L-prolines and the enzymatic activity of the corresponding N-(3-mercapto-2-R-methyl-propionyl) analogs as inhibitors of angiotensin converting enzyme are described.

Method for preparing saxagliptin intermediates

The invention discloses a method for preparing saxagliptin intermediate compounds. The method includes steps of carrying out reaction on compounds I and dibromomethane in ether organic solvents in the presence of acid under the catalytic effects of cuprous catalysts and zinc powder to obtain the saxagliptin intermediate compounds. The method has the advantages of low cost, little environmental pollution, simplicity and convenience in operation and applicability to industrialization.

Structural Properties and Stereochemically Distinct Folding Preferences of 4,5-cis and trans-Methano- L -Proline Oligomers: The Shortest Crystalline PPII-Type Helical Proline-Derived Tetramer

The synthesis, structural properties, and folding patterns of a series of L-proline methanologues represented by cis- and trans-4,5-methano-L-proline amides and their oligomers are reported as revealed by X-ray crystallography, circular dichroism measurements, and DFT calculations. We disclose the first example of a crystalline tetrameric proline congener to exhibit a polyproline II helical conformation. Experimental evidence of PPII-type helical arrangement (both in solution and in the solid state) of cis-4,5-methano-L-proline oligomers is supported by theoretical calculations reflecting the extent of n→π? stabilization of the trans-amide conformation.