86953-79-9

Basic information

• Product Name: 1-Boc-Pyrrolidine
• Synonyms: N-1-BOC-Pyrrolidone;Tert-Butylpyrrolidine-1-Carboxylate;N-BOC-Tetrahydro pyrrole;tert-Butyl pyrrolidine-1-carboxylate, 1-(tert-Butoxycarbonyl)pyrrolidine;1-Pyrrolidinecarboxylic Acid 1,1-DiMethylethyl Ester;NT 0186;N-tert-Butoxycarbonylpyrrolidine;tert-butyl pyrrolidine-1-carboxylate/1-Boc-pyrrolidin
• CAS NO: 86953-79-9
• Molecular Formula: C₉H₁₇NO₂
• Molecular Weight: 171.24
• EINECS: 1312995-182-4
• Product Categories: Pyrrole&Pyrrolidine&Pyrroline
• Mol File: 86953-79-9.mol

Chemical Properties

• Boiling Point: 80 °C0.2 mm Hg(lit.)
• Flash Point: 187 °F
• Appearance: /
• Density: 0.977 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.107mmHg at 25°C
• Refractive Index: n20/D 1.449(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol
• PKA: -1.28±0.20(Predicted)
• BRN: 4664750
• CAS DataBase Reference: 1-Boc-Pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-Pyrrolidine(86953-79-9)
• EPA Substance Registry System: 1-Boc-Pyrrolidine(86953-79-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 86953-79-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Boc-Pyrrolidine is used as a key intermediate in the synthesis of various pharmaceutical compounds for the development of new drugs. Its ability to undergo α'-lithiations and electrophilic substitution reactions makes it a valuable component in the preparation of diastereomers, which are essential for creating enantiomerically pure drugs.
Used in Organic Synthesis:
1-Boc-Pyrrolidine is used as a building block for the synthesis of a wide range of organic compounds, including:
2-aryl-N-boc-pyrrolidines: These compounds are synthesized for their potential applications in medicinal chemistry and as precursors for the development of novel pharmaceutical agents.
Scalemic 2-pyrrolidinylcuprates: These reagents are used in organic synthesis for the formation of carbon-carbon bonds, particularly in the preparation of complex organic molecules.
2-alkenyl-N-Boc-pyrrolidines: These compounds are synthesized for their potential applications in the development of new materials and pharmaceutical agents.
1-deoxycastanospermine: 1-Boc-Pyrrolidine is synthesized as a potential anti-cancer agent, as it has been shown to inhibit glycosidase enzymes involved in cancer cell growth and metastasis.
Methylphenidate analogues: These compounds are synthesized as potential treatments for attention deficit hyperactivity disorder (ADHD) and other cognitive disorders.
(+)-Elaeokanine A: This natural product is synthesized for its potential applications in the development of new drugs, particularly in the treatment of neurodegenerative diseases and cancer.
Overall, 1-Boc-Pyrrolidine plays a crucial role in the synthesis of various organic compounds and pharmaceutical agents, making it an essential component in the fields of organic synthesis and drug development.

InChI:InChI=1/C9H17NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-7H2,1-3H3

Upstream product

• 109-96-6 3-Pyrroline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 123-75-1 pyrrolidine 
• 173300-85-1 N,N'-(di-tert-butoxycarbonyl)-3,4,5,6-tetrahydro-1H-2-pyrimidinethione 
• 41839-96-7 N-(tert-butoxycarbonyl)-succinimide 
• 62-53-3 aniline 
• 69610-41-9 Boc-L-Pro-H 
• 72925-16-7 1-boc-pyrrolidine-3-carboxylic acid 
• 24608-52-4 tert-butyl chloroformate 
• 201230-82-2 carbon monoxide 
• 75-65-0 tert-butyl alcohol 
• 170491-63-1 N-Boc-prolinol 
• 73286-70-1 N-(tert-butoxycarbonyl)-3-pyrroline 
• 151259-38-0 tert-butyl diallylcarbamate 

Downstream Products

• 137496-71-0 2-methylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 157007-54-0 2-(R)-methylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 214400-41-6 (R)-2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 146337-04-4 N-[(1,1-dimethylethoxy)carbonyl]-2-(2-propen-1-yl)pyrrolidine 
• 190734-80-6 (Z)-ethyl 3-[[(1,1-dimethylethoxy)carbonyl]-2-pyrrolidinyl]-2-heptenoate 

Relevant articles and documents

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Strong and confined imidodiphosphorimidate (IDPi) catalysts enable highly enantioselective substitutions of cyclic, aliphatic hemiaminal ethers with enol silanes. 2-Substituted pyrrolidines, piperidines, and azepanes are obtained with high enantioselectiv

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Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners

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Sustainable Route Toward N-Boc Amines: AuCl3/CuI-Catalyzed N-tert-butyloxycarbonylation of Amines at Room Temperature

N-tert-butoxycarbonyl (N-Boc) amines are useful intermediates in synthetic/medicinal chemistry. Traditionally, they are prepared via an indirect phosgene route with poor atom economy. Herein, a step- and atom-economic synthesis of N-Boc amines from amines, t-butanol, and CO was reported at room temperature. Notably, this N-tert-butyloxycarbonylation procedure utilized ready-made substrates, commercially available AuCl3/CuI as catalysts, and O2 from air as the sole oxidant. This catalytic system provided unique selectivity for N-Boc amines in good yields. More significantly, gram-scale preparation of medicinally important N-Boc amine intermediates was successfully implement, which demonstrated a potential application prospect in industrial syntheses. Furthermore, this approach also showed good compatibility with tertiary and other useful alcohols. Investigations of the mechanisms revealed that gold catalyzed the reaction and copper acted as electron transfer mediator in the catalytic cycle.

Iron-Catalyzed C-C Single-Bond Cleavage of Alcohols

An iron-catalyzed deconstruction/hydrogenation reaction of alcohols through C-C bond cleavage is developed through photocatalysis, to produce ketones or aldehydes as the products. Tertiary, secondary, and primary alcohols bearing a wide range of substituents are suitable substrates. Complex natural alcohols can also perform the transformation selectively. A investigation of the mechanism reveals a procedure that involves chlorine radical improved O-H homolysis, with the assistance of 2,4,6-collidine.

Synthesis of Amide Enol Carbamates and Carbonates through Cu(OTf)2-Catalyzed Reactions of Ynamides with t-Butyl Carbamates/Carbonates

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Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer

We report a catalytic, light-driven method for the intramolecular hydroetherification of unactivated alkenols to furnish cyclic ether products. These reactions occur under visible-light irradiation in the presence of an IrIII-based photoredox catalyst, a Br?nsted base catalyst, and a hydrogen-atom transfer (HAT) co-catalyst. Reactive alkoxy radicals are proposed as key intermediates, generated by direct homolytic activation of alcohol O?H bonds through a proton-coupled electron-transfer mechanism. This method exhibits a broad substrate scope and high functional-group tolerance, and it accommodates a diverse range of alkene substitution patterns. Results demonstrating the extension of this catalytic system to carboetherification reactions are also presented.

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Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration

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Hydrogenation reaction method

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