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

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

Uses

Used in Organic Synthesis:
(S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, making it a versatile building block for creating complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate is used as a precursor for the synthesis of novel drug candidates, leveraging its potential biological activities and its role as a chiral ligand in catalytic reactions to enhance the development of new medications.

Upstream product

• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 69610-41-9 Boc-L-Pro-H 
• 593-60-2 Vinyl bromide 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 1354376-12-7 (S)-tert-butyl 2-[(R)-1-hydroxy-(trimethylsilyl)ethyl]pyrrolidine-1-carboxylate 
• 856015-54-8 (E)-6-aminohex-2-en-1-ol 
• 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 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 105838-14-0 tert-butyl N-tosyloxycarbamate 

Downstream Products

• 105706-79-4 N-chloroacetyl-2-vinylpyrrolidine 
• 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 

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 convenient entry to indolizidine alkaloids using Kharasch type reactions

A convenient entry to indolizidine alkaloids based on a free-radical atom transfer reaction (ATRA or Kharasch reaction) as the key step is reported. The strategy is based on the free radical reaction between ethyl iodoacetate and an l-proline derivative serving as a radical acceptor. The key intermediate obtained after the radical reaction is used for the synthesis of indolizidine (-)-167B and of an advanced intermediate for the synthesis of (+)-dendroprimine.

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.

Construction of chiral 1,2-cycloalkanopyrrolidines from L-proline using ring closing metathesis (RCM)

An efficient synthetic method for the preparation of optically active pyrroloazocine, pyrroloazepine, quinolizidine, indolizidine using ring closing olefin metathesis (RCM) is described.

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.

Chiron approach to (-)-deoxocuscohygrine

A facile chiron approach to C2-symmetrical (-)-deoxocuscohygrine is described by using cross metathesis as the key step.

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.

A One-Pot Iodo-Cyclization/Transition Metal-Catalyzed Cross-Coupling Sequence: Synthesis of Substituted Oxazolidin-2-ones from N-Boc-allylamines

A one-pot iodo-cyclization/transition metal-catalyzed cross-coupling sequence is reported to access various C5-functionalized oxazolidin-2-ones from unsaturated N-Boc-allylamines. Depending on the Grignard reagents used for the cross-coupling, e.g., aryl- or cyclopropylmagnesium bromide, a cobalt or copper catalyst has to be used to obtain the functionalized oxazolidin-2-ones in good yields.

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.

Synthesis of γ-Lactams by Mild, o-Benzoquinone-Induced Oxidation of Pyrrolidines Containing Oxidation-Sensitive Functional Groups

The late-stage oxidation of substituted pyrrolidines offers good flexibility for the construction of γ-lactam libraries, and especially in recent years the methods for functionalization of pyrrolidine have been available. We reported a new strategy for oxidation of pyrrolidines to γ-lactams: reaction of pyrrolidine with an o-benzoquinone gives an N,O-acetal by direct oxidation of the α-C-H bond of the pyrrolidine ring, and then the N,O-acetal is further oxidized by the o-benzoquinone to the γ-lactam. Because the first oxidation occurs selectively at the α-C-H of the pyrrolidine ring, oxidation-sensitive functional groups (allyl-, vinyl-, hydroxyl-, and amino groups) on pyrrolidine ring are unaffected. The synthetic utility of this novel method was demonstrated by the facile syntheses of (S)-vigabatrin and two analogues.