116183-82-5

Basic information

• Product Name: (R)-3-Aminopyrrolidine
• Synonyms: (3R)-Pyrrolidine-3-amine;(3R)-pyrrolidin-3-aMine;(r)-(R)-3-AMinopyrrolidine;(R)-(+)-3-Aminopyrrolidine 98%;(3R)-(+)-AMINOPYRROLIDINE;(3R)-()-3-AMINOPYRROLIDINE;(3R)-(+)-3-AMINOPYRROLIDINE;R-AP
• CAS NO: 116183-82-5
• Molecular Formula: C₄H₁₀N₂
• Molecular Weight: 86.14
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Pyrrolidines;pharmacetical;Pyrrole&Pyrrolidine&Pyrroline;API intermediates;3-Aminopyrrolidines;Amines (Chiral);Chiral 3-Aminopyrrolidines;Chiral Building Blocks;Synthetic Organic Chemistry;Chiral Compound
• Mol File: 116183-82-5.mol

Chemical Properties

• Boiling Point: 164-165 °C(lit.)
• Flash Point: 147 °F
• Appearance: /
• Density: 0.984 g/mL at 25 °C(lit.)
• Vapor Pressure: 8.95mmHg at 25°C
• Refractive Index: n20/D 1.489(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 9.94±0.20(Predicted)
• CAS DataBase Reference: (R)-3-Aminopyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-Aminopyrrolidine(116183-82-5)
• EPA Substance Registry System: (R)-3-Aminopyrrolidine(116183-82-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 116183-82-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-Aminopyrrolidine is used as a key intermediate in the synthesis of various drugs and drug intermediates, contributing to the development of new therapeutic agents.
Used in Organic Chemistry:
(R)-3-Aminopyrrolidine is utilized as a building block in organic synthesis, enabling the creation of complex organic molecules for research and commercial applications.
Used in Catalysis:
(R)-3-Aminopyrrolidine is employed as a catalyst or catalyst precursor in various chemical reactions, enhancing reaction efficiency and selectivity.

InChI:InChI=1/C4H10N2/c5-4-1-2-6-3-4/h4,6H,1-3,5H2/t4-/m1/s1

Upstream product

• 114715-38-7 (3S)-1-benzyl-3-pyrrolidinamine 
• 56440-28-9 (S)-3-amino-2-pyrrolidinone hydrochloride 
• 79286-79-6 pyrrolidin-3-amine 
• 945483-29-4 (3R,αS)-N(1)-benzyl-3-[N'-benzyl-N'-(α-methylbenzyl)amino]pyrrolidine 
• 404887-22-5 3-aminopyrrolidine-2,5-dione 
• 122536-76-9 3(S)-(tert-butoxycarbonylamino)pyrrolidine 

Downstream Products

• 132195-48-3 7-((S)-3-Amino-pyrrolidin-1-yl)-6-fluoro-1-(4-fluoro-phenyl)-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 
• 146560-56-7 7-((S)-3-Amino-pyrrolidin-1-yl)-6-fluoro-1-(4-methoxy-phenyl)-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 
• 146560-54-5 7-((S)-3-Amino-pyrrolidin-1-yl)-6-fluoro-1-(4-fluoro-2-methoxy-phenyl)-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 
• 146560-55-6 7-((S)-3-Amino-pyrrolidin-1-yl)-6-fluoro-1-(2-fluoro-4-methoxy-phenyl)-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 
• 179739-88-9 1-(3-amino-2,4-difluorophenyl)-7-[(3S)-3-aminopyrrolidin-1-yl]-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid 
• 956468-08-9 N-((3S)-1-{[3,4-bis(methyloxy)phenyl]sulfonyl}-3-pyrrolidinyl)-3,4-bis(methyloxy)benzenesulfonamide 
• 749844-54-0 (S) 8-(3-aminopyrrolidin-1-yl)-7-(2-bromobenzyl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione 
• 485820-45-9 (S) 8-(3-aminopyrrolidin-1-yl)-7-(2-bromobenzyl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione hydrochloride 
• 99724-19-3 3-(tert-butoxycarbonylamino)pyrrolidine 
• 147081-44-5 (3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine 

Relevant articles and documents

Synthesis of 6-oxopyrimidin-1(6H)-yl benzamide derivatives and evaluation of their antibacterial and cytotoxic activity

A series of novel 2-alkylamino and 2, 4-dialkyl amino 6-oxopyrimidin-1(6H)-yl) benzamide derivatives were prepared in good yields from a base-catalyzed ring opening of oxadiazolo[3,2-a]pyrimidin-5-one and evaluated for their antibacterial and cytotoxicity. Most of the compounds exhibited antibacterial activity. In particular, compounds 5b and 5k exhibited considerable antibiotic activity against Klebsiella pneumonia and Bacillus cereus. In addition, compounds 5g and 5i also inhibited the growth of two human tumor cell lines (A549 and H460) at micromolar concentrations.

Preparation method of ceftobiprole ester intermediate (R)-1-tert-butyloxycarbonyl-3-aminopyrrolidine

The invention discloses a preparation method of (R)-1-tert-butyloxycarbonyl-3-aminopyrrolidine. The method comprises the following steps: 1, carrying out a reaction on (D) asparagine with thionyl chloride/methanol to generate D-asparagine methyl ester hydrochloride; protecting the amino group of the D-aspartic acid methyl ester hydrochloride by using di-tert-butyl dicarbonate; carrying out a ringclosing reaction by using sodium hydride, removing BOC anhydride protection of 3-amino by using TFA, and then reducing the diketone at the 2 and 5 sites by using sodium borohydride; finally protecting1-imino by using di-tert-butyl dicarbonate to obtain an yellow oily substance, (R)-1-tert-butyloxycarbonyl-3-aminopyrrolidine. The method is low in cost, small in pollution, easy to operate and beneficial to industrial production, the purity of the product can reach 98%, and a guarantee is provided for subsequent synthesis of high-purity cefepime.

Enantioselective Synthesis of 2-Aminomethyl and 3-Amino Pyrrolidines and Piperidines through 1,2-Diamination of Aldehydes

An efficient method for the synthesis of 1,2-diamines from aldehydes through proline-catalyzed asymmetric α-amination followed by reductive amination is reported. The products resemble those obtained through direct asymmetric diamination of terminal alkenes. The methodology is used to synthesize 2-aminomethyl and 3-amino pyrrolidines and piperidines in high yields and with a good enantioselectivity. The usefulness of the method is demonstrated through the synthesis of a 2-aminomethyl iminocyclitol.

A protection strategy substantially enhances rate and enantioselectivity in ω-transaminase-catalyzed kinetic resolutions

The kinetic resolution of 3-aminopyrrolidine (3AP) and 3-aminopiperidine (3APi) with ω-transaminases was facilitated by the application of a protecting group concept. 1-N-Cbz-protected 3-aminopyrrolidine could be resolved with >99% ee at 50% conversion, the resolution of 1-N-Boc-3-aminopiperidine yielded 96% ee at 55% conversion. The reaction rate was up to 50-fold higher by using protected substrates. Most importantly, enantioselectivity increased remarkably after carbamate protection compared to the unprotected substrates (86 vs. 99% ee). Surprisingly, benzyl protection of 3AP had no influence on enantioselectivity. A possible explanation for this observation could be the different flexibility of the benzyl- or carbamate-protected 3AP as confirmed by NMR spectroscopy.

Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition

The diastereoselective conjugate addition of homochiral lithium amides to methyl 4-(N-allyl-N-benzylamino)but-2-enoate has been used as the key step in a simple and efficient protocol for the preparation of 3,4-substituted aminopyrrolidines. This protocol provides a complementary and stereoselective route to both anti- and syn-3-amino-4-alkylpyrrolidines as well as anti- and syn-3-hydroxy-4-aminopyrrolidines, in high de and ee via β-amino enolate functionalisation. This methodology has been applied to the synthesis of anti-(3S,4S)- and syn-(3R,4S)-3-methoxy-4-(N-methylamino)pyrrolidine. The Royal Society of Chemistry.

Lithium amide conjugate addition for the asymmetric synthesis of 3-aminopyrrolidines

Conjugate addition of homochiral lithium amides to methyl 4-(N-benzyl-N-allylamino)but-2-enoate, chemoselective N-deprotection and concomitant cyclisation, followed by enolate functionalisation and deprotection allows access to syn- and anti-3,4-disubstituted aminopyrrolidines in > 98% d.e. and > 98% e.e. The Royal Society of Chemistry 2006.

PROCESS FOR PRODUCING NITROGENOUS HETEROCYCLIC COMPOUND

A nitrogenous heterocyclic compound such as 3-aminopyrrolidine derivative is produced by hydrogenolysis of an N-substituted nitrogenous heterocyclic compound with normal pressure hydrogen in a water-based solvent in presence of a catalyst. In the case an optically active 1-substituted-3-aminopyrrrolidine derivative is used as a raw material, an optically active 3-aminopyrrolidine derivative can be obtained as a product practically without racemination.

Process for producing 1H-3-aminopyrrolidine and derivatives thereof

A process for producing 1H-3-aminopyrrolidine and derivatives thereof is disclosed. The process is especially useful for producing optically active 1H-3-aminopyrrolidine and derivatives thereof and in this case comprises reacting an optically active amino-protected aspartic anhydride represented by the formula (1) with a primary amine represented by the formula R'NH2, subjecting the reaction product to cyclodehydration to obtain an optically active 1-aralkyl-3-(protected amino)pyrrolidine-2,5-dione compound represented by the formula (2), subsequently eliminating the protective group from the 3-position amino group of the compound represented by the formula (2) to obtain an optically active 1-aralkyl-3-aminopyrrolidine-2,5-dione compound represented by the formula (3), reducing the carbonyl groups of the compound represented by the formula (3) to obtain either an optically active 1-aralkyl-3-aminopyrrolidine compound represented by the formula (4) or a salt thereof with a protonic acid, and then subjecting the compound represented by the formula (4) or the salt thereof to hydrogenolysis to obtain an optically active 1H-3-aminopyrrolidine or a protonic acid salt thereof.

Methods for making optically active 3-aminopyrrolidine-2,5-dione derivative and optically active 3-aminopyrrolidine derivative

A method for making an optically active 3-aminopyrrolidine-2,5-dione derivative represented by the formula (3) includes cyclizing an optically active asparagine ester derivative represented by the formula (1) or (2), or an acid salt thereof. A method for making an optically active 3-aminopyrrolidine derivative represented by the formula (9) includes reducing the optically active 3-aminopyrrolidine-2,5-dione derivative represented by the formula (3). A method for making an optically active 3-aminopyrrolidine derivative includes hydrogenolyzing the optically active 3-aminopyrrolidine derivative represented by the formula (9).

Methods for making optically active 3-aminopyrrolidine-2,5-dione derivative and optically active 3-aminopyrrolidine derivative

A method for making an optically active 3-aminopyrrolidine-2,5-dione derivative represented by the formula (3) includes cyclizing an optically active asparagine ester derivative represented by the formula (1) or (2) or an acid salt thereof. The optically active 3-aminopyrrolidine-2,5-dione derivative represented by the formula (3) may be reduced to form an optically active 3-aminopyrrolidine derivative represented by the formula (9). When, in the formula (9), R1 is an unsubstituted or substituted benzyl group, the compound may be hydrogenated to obtain the corresponding 1-unsubstituted compound in which R1 is hydrogen.