115393-77-6

Basic information

• Product Name: (S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate
• Synonyms: (S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate
• CAS NO: 115393-77-6
• Molecular Formula: C₁₁H₁₉NO₂
• Molecular Weight: 197.27406
• Mol File: 115393-77-6.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 248.4±29.0 °C(Predicted)
• Appearance: /
• Density: 1.050±0.06 g/cm3(Predicted)
• PKA: -1.99±0.40(Predicted)
• CAS DataBase Reference: (S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate(115393-77-6)
• EPA Substance Registry System: (S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate(115393-77-6)

Safety Data

• Hazardous Substances Data: 115393-77-6(Hazardous Substances Data)

Usage

General Description

(S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate is a chemical compound with the molecular formula C11H19NO2. It is a tert-butyl ester of (S)-2-vinylpyrrolidine-1-carboxylic acid, and is commonly used as a reagent in organic synthesis and pharmaceutical research. (S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate is known for its ability to undergo various chemical reactions, such as Michael additions and radical polymerizations, making it a versatile building block for the synthesis of complex organic molecules. Additionally, (S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate has been studied for its potential biological activities, including its role as a chiral ligand in catalytic reactions and as a precursor for the synthesis of novel drug candidates. Overall, this chemical exhibits promising applications in both the chemical and pharmaceutical industries.

Upstream product

• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 69610-41-9 Boc-L-Pro-H 
• 19493-09-5 Methylenetriphenylphosphorane 
• 220926-82-9 N-(tert-butoxycarbonyl)-N-(3-chloropropyl)allylamine 
• 593-60-2 Vinyl bromide 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 593-66-8 vinyliodide 
• 78888-18-3 N-tert-butoxycarbonylprop-2-en-1-amine 
• 1353722-73-2 6-((tert-butoxycarbonyl)amino)-1-((tert-butyldimethylsilyl)oxy)hex-2-yne 
• 24424-99-5 di-tert-butyl dicarbonate 
• 128773-83-1 6-azidohex-2-yn-1-ol 
• 1008751-38-9 (E)-6-((tert-butoxycarbonyl)amino)hex-2-en-1-ol 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 

Downstream Products

• 175022-84-1 (S)-1-(o-iodobenzoyl)-2-vinylpyrrolidine 
• 175022-83-0 (S)-1-(o-iodobenzoyl)-2-vinylpyrrolidine 
• 880634-64-0 2-diazo-3-oxo-5-[(2S)-2-vinylpyrrolidin-1-yl]pentanoic acid (-)-mentyl ester 
• 880634-63-9 2-diazo-3-oxo-5-[(2S)-2-vinylpyrrolidin-1-yl]pentanoic acid benzyl ester 
• 876617-06-0 tert-butyl (2R)-2-ethylpyrrolidine-1-carboxylate 
• 1312700-28-9 (S)-7-(benzyloxymethyl)-2,3-dihydro-1H-pyrrolizin-5(7aH)-one 
• 1312700-22-3 (S)-1-(2-(3-(benzyloxy)prop-1-en-2-yl)pyrrolidin-1-yl)but-3-en-1-one 
• 1312700-31-4 (S)-8-(benzyloxymethyl)-1,2,3,8a-tetrahydroindolizin-5(6H)-one 
• 1312700-32-5 ((8S,8aS)-5-oxo-octahydroindolizin-8-yl)methyl benzoate 
• 1312700-29-0 ((1S,7aS)-3-oxohexahydro-1H-pyrrolizin-1-yl)methyl benzoate 
• 1312700-30-3 ((1R,7aS)-3-oxohexahydro-1H-pyrrolizin-1-yl)methyl benzoate 
• 1312700-26-7 tert-butyl (S)-2-(2-(benzyloxy)acetyl)pyrrolidine-1-carboxylate 
• 1312700-27-8 tert-butyl (S)-2-(3-(benzyloxy) prop-1-en-2-yl)pyrrolidine-1-carboxylate 
• 1312700-23-4 (S)-2-(3-(benzyloxy)prop-1-en-2-yl)pyrrolidine 

Relevant articles and documents

Stereocontrolled Total Synthesis of (?)-Stemaphylline

Homologation of readily available α-boryl pyrrolidines with metal carbenoids is especially challenging even when good leaving groups (Cl?) are employed. By performing a solvent switch from Et2O to CHCl3, efficient 1,2-metalate rearrangement of the intermediate boronate occurs with both halide and ester leaving groups. The methodology was used in the total synthesis of the Stemona alkaloid (?)-stemaphylline in just 11 steps (longest linear sequence), with high stereocontrol (>20:1 d.r.) and 11 % overall yield. The synthesis also features a late-stage lithiation–borylation reaction with a tertiary amine containing carbenoid.

A highly efficient conversion of a simple derivative of the amino acid proline into a nearly enantiomerically pure n-protected allyl amine: Use of thionyl chloride to promote the Peterson olefination

A novel two-step conversion of an N-Boc methyl ester of the natural amino acid proline into highly enantioenriched N-Boc 2-vinylpyrrolidine is described. Key steps include (1) an SNi displacement of a methoxy group of the DIBAL-H adduct of the starting ester by the TMSCH2 group of the corresponding Grignard reagent, and (2) the use of thionyl chloride to promote the Peterson olefination of the resulting -hydroxysilane bearing a stereocenter adjacent to the alcohol function. The overall transformation occurs with remarkable facility and virtually without loss of stereochemical integrity under mild conditions. The use of thionyl chloride in the elimination step is necessary because both basic and acidic conditions are incompatible with the Boc protecting group. In stark contrast to the standard Wittig olefination of the corresponding N-protected amino aldehyde, where 8-10% racemization (80-84% ee) occurs, only about 1% racemization (98% ee) was observed in this novel process. Georg Thieme Verlag Stuttgart · New York.

A metallocarbenoid approach to the formation of spirocyclic ammonium ylides leading to the preparation of medium-sized azacane rings

A novel approach to azacyclooctene and azacyclononene containing substrates has been achieved via the intermediacy of a spirocyclic ammonium ylide derived from the diazodecomposition of a tethered α-diazoester moiety.

BIARYL DERIVATIVES AS YAP/TAZ-TEAD PROTEIN-PROTEIN INTERACTION INHIBITORS

The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof; (I) a method for manufacturing said compound, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition comprising said compound.

Enantioselective Aza-Heck Cyclizations of N-(Tosyloxy)carbamates: Synthesis of Pyrrolidines and Piperidines

Pd(0)-systems modified with SPINOL-derived phosphoramidate ligands promote highly enantioselective aza-Heck cyclizations of alkenyl N-(tosyloxy)carbamates. The method provides versatile access to challenging N-heterocycles and represents the broadest scope enantioselective aza-Heck protocol developed to date.