84348-38-9

Basic information

• Product Name: (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
• Synonyms: 1,2-Pyrrolidinedicarboxylicacid, 4-Methylene-, 1-(1,1-diMethylethyl) ester, (2S)-;(S)-1-(tert-butoxycarbonyl)-4-Methylenepyrrolidine-2-carboxylic acid;N-tert-Butoxycarbonyl-4-methylene-L-proline;N-Boc-4-methylene-L-proline 97%;N-T-BOC-4-METHYLENE-L-PROLINE;(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER;BOC-4-METHYLENE-L-PROLINE;N-Boc-4-methylene-L-proline
• CAS NO: 84348-38-9
• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.26
• Product Categories: Heterocycles;pharmacetical
• Mol File: 84348-38-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 110-114°C
• Boiling Point: 349.859 °C at 760 mmHg
• Flash Point: 165.389 °C
• Appearance: /
• Density: 1.18±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.80±0.20(Predicted)
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER(84348-38-9)
• EPA Substance Registry System: (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER(84348-38-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 84348-38-9(Hazardous Substances Data)

Usage

Description

(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER is a chiral compound that serves as an important intermediate in various chemical and pharmaceutical applications. It is derived from the commercially available N-Boc-4-methylene-L-proline and is known for its unique structure and properties.

Uses

Used in Peptide Synthesis:
(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER is used as a key building block in peptide synthesis, allowing for the creation of complex peptide structures with specific biological activities.
Used in Asymmetric Synthesis:
In asymmetric synthesis, (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER is employed as a chiral auxiliary, helping to control the stereochemistry of reactions and produce enantiomerically pure products.
Used in Medicinal Chemistry:
(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER is utilized in medicinal chemistry as a versatile intermediate for the development of novel pharmaceutical compounds, particularly those targeting specific biological receptors or pathways.
Used in Polymer Chemistry:
In the field of polymer chemistry, (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER is used as a monomer or building block for the synthesis of functional polymers with tailored properties, such as chiral polymers with specific recognition or binding capabilities.
Used in Fluorous Prolinol Synthesis:
(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER is used as a starting material for the synthesis of fluorous prolins, which are valuable reagents in organic synthesis and catalysis, offering unique properties due to their fluorous tags.

InChI:InChI=1/C11H17NO4/c1-7-5-8(9(13)14)12(6-7)10(15)16-11(2,3)4/h8H,1,5-6H2,2-4H3,(H,13,14)/t8-/m0/s1

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 163190-46-3 tert-Butyl (2S)-N-tert-butoxycarbonyl-4-methylideneprolinate 
• 144423-03-0 N-phenylsulphonyl-N-propargyl-O-tetrahydropyranyl-(S)-serine benzylester 
• 144422-80-0 N-phenylsulphonyl-N-propargyl-3-bromo-(S)-alanine benzylester 
• 144422-81-1 N-phenylsulphonyl-4-exomethylene-(S)-proline benzylester 
• 20309-87-9 (2S)-4-methylenepyrrolidine-2-carboxylic acid 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 27200-84-6 methyl triphenylphosphonium bromide 
• 84348-39-0 (S)-1-tert-butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate 

Downstream Products

• 84348-39-0 (S)-1-tert-butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate 
• 1129634-44-1 (6S)-5-[(tert-butoxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acid 
• 1129634-43-0 (6S)-5-tert-butyl 6-methyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate 
• 1499193-61-1 (S)-6-(2-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-2-oxoethyl) 5-tert-butyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate 
• 1441670-89-8 (6S)-6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptane-5-carboxylic acid 1,1-dimethylethyl ester 
• 928063-63-2 C₂₃H₃₀N₂O₆ 
• 928063-88-1 C₂₂H₃₀N₂O₅ 
• 1296797-07-3 C₈H₁₃NO₂*ClH 
• 364750-81-2 N-tert-Butyloxycarbonyl-(2S,4S)-4-methylproline 
• 1029798-76-2 (S)-2-[4-(4-cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-4-methylene-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 84348-40-3 methyl 4-methylene-L-proline 
• 84348-41-4 (S)-methyl 4-methylenepyrrolidine-2-carboxylate hydrochloride 

Relevant articles and documents

An enantioselective approach to 4-substituted proline scaffolds: Synthesis of (s)-5-(tert-butoxy carbonyl)-5-azaspiro[2.4]heptane-6-carboxylic acid

A catalytic and enantioselective preparation of the (S)-4-methyleneproline scaffold is described. The key reaction is a one-pot double allylic alkylation of an imine analogue of glycine in the presence of a chinchonidine-derived catalyst under phase transfer conditions. These 4-methylene substituted proline derivatives are versatile starting materials often used in medicinal chemistry. In particular, we have transformed tert-butyl (S)-4-methyleneprolinate (12) into the N-Boc-protected 5-azaspiro[2.4]heptane-6-carboxylic acid (1), a key element in the industrial synthesis of antiviral ledipasvir.

Ledipasvir preparation method

The invention discloses a Ledipasvir preparation method. The Ledipasvir preparation method includes steps: (1) Ledipasvir intermediate product 1-LD-B preparation; (2) Ledipasvir intermediate product 2-LD-E preparation; (3) Ledipasvir intermediate product 3-LD-F preparation; (4) Ledipasvir intermediate product 4-LD-J preparation; (5) Ledipasvir intermediate product 5-LD-L preparation; (6) Ledipasvir-LD-Q preparation. The Ledipasvir preparation method has advantages of technical maturity and stability, product quality stability, safety and reliability in production process and suitableness for industrial production.

DIHYDROPYRIMIDINE COMPOUNDS AND THEIR APPLICATION IN PHARMACEUTICALS

Provided herein are dihydropyrimidine compounds and their pharmaceutical applications, especially for use in treating and preventing HBV diseases. Specifically, provided herein are compounds having Formula (I) or (Ia), or an enantiomer, a diastereoisomer,