147081-49-0

Basic information

• Product Name: (R)-(+)-1-Boc-3-aminopyrrolidine
• Synonyms: 1-PYRROLIDINECARBOXYLIC ACID, 3-AMINO-, 1,1-DIMETHYLETHYL ESTER, (3R);3-AMINO-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER, (R);(R)-TERT-BUTYL 3-AMINOPYRROLIDINE-1-CARBOXYLATE;(R)-(+)-N-BOC-3-AMINOPYRROLIDINE;(R)-(+)-N-tert-Butoxycarbonyl-3-aminopyrrolidine;TERT-BUTYL (3R)-3-AMINOPYRROLIDINE-1-CARBOXYLATE;(R)-3-AMINO-1-BOC-PYRROLIDINE;(R)-3-AMINO-1-N-(T-BUTOXYCARBONYL)PYRROLIDINE
• CAS NO: 147081-49-0
• Molecular Formula: C₉H₁₈N₂O₂
• Molecular Weight: 186.25
• Product Categories: pharmacetical;chiral;Pyrrole&Pyrrolidine&Pyrroline;Benzenes;3-Aminopyrrolidines;Chiral 3-Aminopyrrolidines
• Mol File: 147081-49-0.mol

Chemical Properties

• Melting Point: 243-244°C
• Boiling Point: 243-244°C
• Flash Point: 196°F
• Appearance: Clear pale yellow/Liquid
• Density: 1.098
• Refractive Index: 1.4720
• Storage Temp.: Room temperature.
• PKA: 9.55±0.20(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: (R)-(+)-1-Boc-3-aminopyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1-Boc-3-aminopyrrolidine(147081-49-0)
• EPA Substance Registry System: (R)-(+)-1-Boc-3-aminopyrrolidine(147081-49-0)

Safety Data

• Hazard Codes: C,Xn
• Statements: 22-41-44
• Safety Statements: 26-36/37/39
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: Ⅲ
• Hazardous Substances Data: 147081-49-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-1-Boc-3-aminopyrrolidine is used as a key intermediate for the synthesis of various pharmaceutical compounds, such as Descarboxamide analog and Na-methylated analogs of 4-N-(Nω-nitro-L-argininyl)-trans-4-amino-L-proline amide. These analogs have potential applications in the development of new drugs targeting specific biological pathways.
Used in Medicinal Chemistry:
(R)-(+)-1-Boc-3-aminopyrrolidine is used as a building block for the development of Histamine 3 (H3) receptor antagonists containing a pyrrolidin-3-yl-N-methylbenzamide moiety. These antagonists play a crucial role in the treatment of various conditions, such as cognitive disorders, attention deficit hyperactivity disorder (ADHD), and Alzheimer's disease, by modulating the histamine signaling pathway.
Used in Chemical Synthesis:
(R)-(+)-1-Boc-3-aminopyrrolidine is used as a versatile chiral building block in the synthesis of various organic compounds, including natural products, pharmaceuticals, and agrochemicals. Its unique structure and reactivity make it a valuable asset in the development of novel molecules with potential applications in various industries.

InChI:InChI=1/C9H18N2O2.ClH/c1-9(2,3)13-8(12)11-5-4-7(10)6-11;/h7H,4-6,10H2,1-3H3;1H/t7-;/m1./s1

Upstream product

• 945483-28-3 (3R,αS)-N(1)-tert-butyloxycarbonyl-3-[N'-benzyl-N'-(α-methylbenzyl)amino]pyrrolidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 116183-82-5 (R)-pyrrolidin-3-amine 
• 1013-88-3 Benzophenone imine 
• 186550-13-0 3-amino-1-(t-butoxycarbonyl)pyrrolidine 
• 132945-75-6 (S)-tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate 
• 1004538-27-5 (R)-1-(tert-butoxycarbonyl)-3-aminopyrrolidine acetate 
• 143700-04-3 (R)-tert-butyl 3-azidopyrrolidine-1-carboxylate 
• 371240-55-0 (S)-3-(toluene-4-sulfonyloxy)pyrrolidin-1-ylcarboxylic acid tert-butyl ester 
• 101469-92-5 (S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 247569-07-9 (R)-tert-butyl 3-(benzyloxycarbonylamino)pyrrolidine-1-carboxylate 

Downstream Products

• 348165-98-0 tert-butyl (R)-3-(4-(5-carbamoyl-2-methylphenylamino)-6-chloro-1,3,5-triazin-2-ylamino)pyrrolidine-1-carboxylate 
• 1026000-70-3 (R)-3-{4-(5-Carbamoyl-2-methyl-phenylamino)-6-[((1S,2R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 936115-76-3 3-[(pyridin-2-ylmethyl)-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 936115-74-1 3-(cyclopropylmethyl-amino)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 717927-57-6 tert-butyl (R)-3-(4-benzylpiperazin-1-yl)pyrrolidine-1-carboxylate 
• 1016641-56-7 C₂₅H₂₅N₅O₅ 
• 1000370-76-2 tert-butyl (R)-3-((2-nitrophenyl)amino)pyrrolidine-1-carboxylate 
• 816464-41-2 tert-butyl (3R)-3-[({3-[(2,4-difluorophenyl)amino]-6-oxo-7-phenyl-6,7-dihydrothieno[2,3-b]pyridin-2-yl}carbonyl)amino]pyrrolidine-1-carboxylate 
• 247569-13-7 (R)-2-[1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino]-5-cyano-N-(3,4-dimethoxybenzyl)benzamide 
• 887587-15-7 3-ethylamino-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 849106-80-5 3-(4-chloro-benzylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 849107-06-8 3-(methoxycarbonylmethyl-amino)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1000592-70-0 C₁₅H₂₁IN₂O₄S 
• 1024582-78-2 (3S)-tert-butyl 3-(2-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenoxy)acetamido)pyrrolidine-1-carboxylate 

Relevant articles and documents

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.

HETEROAROMATIC DERIVATIVES AND PHARMACEUTICAL APPLICATIONS THEREOF

Disclosed are heteroaryl derivatives, pharmaceutical composition and uses in the manufacture of a medicine for treating respiratory diseases, especially for chronic obstructive pulmonary disease (COPD).

Aromatic heterocyclic derivatives and applications of aromatic heterocyclic derivatives in medicines

The present invention discloses aromatic heterocyclic derivatives and applications of the aromatic heterocyclic derivatives in medicines, and specifically provides a class of aromatic heterocyclic compounds or stereoisomers, geometric isomers, tautomers, racemic bodies, nitrogen oxides, hydrates, solvates, metabolites, pharmaceutically acceptable salts or prodrugs thereof, and pharmaceutical compositions containing the compounds. The present invention further discloses uses of the compounds or pharmaceutical compositions in drug preparation, wherein the drug is used for treatment of respiratory diseases, particularly chronic obstructive pulmonary disease (COPD).

CARBAPENEM ANTIBACTERIALS WITH GRAM-NEGATIVE ACTIVITY

The present invention provides β-methyl carbapenem compounds and pharmaceutical compositions useful in the treatment of bacterial infections and methods for treating such infections using such compounds and/or compositions. The invention includes administering an effective amount of a carbapenem compound or salt and/or prodrug thereof to a host in need of such a treatment.

METHOD FOR PRODUCTION OF OPTICALLY ACTIVE 3-AMINO-NITROGENATED COMPOUND

Aiming at production of an optically active 3-amino nitrogen-containing compound which is useful as an intermediate in synthesis of medicines and pesticides, in particular, an optically active 1-protected-3-aminopyrrolidine derivative, from an inexpensive and readily available raw material by a process which is efficient and can be practiced industrially, an optically active 3-amino nitrogen-containing compound is produced by performing a reaction of an optically active 3-substituted nitrogen-containing compound with ammonia, methylamine, ethylamine or dimethylamine in the presence of water. In addition, a 1-protected-3-aminopyrrolidine derivative is produced by performing a reaction of an optically active 1-protected-3-(sulfonyloxy)pyrrolidine derivative with ammonia, methylamine, ethylamine, or dimethylamine in the presence of methanol, ethanol, n-propanol, or isopropanol under a pressure of less than 30 barr.

NOVEL 7-SUBSTITUTED 3-CARBOXY-OXADIAZINO-QUINOLONE DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATION AS ANTI-BACTERIALS

A subject of the invention is the compounds of formula (I): in which either R1 represents H, OH, NH2, —(CH2)m—NRaRb(m=0.1 or 2),Ra and Rb represent H, linear, branched or cyclic (C1 -C6) alkyl, (C3-C6) cycloalkyl-(C3-C6)— alkyl, Rc, S(O)2Rc, C(O)Rc, S(O)2Rd or C(O)Rd;or Ra and Rb with N form an Rc radical;Rc represents a saturated, unsaturated or 5- or 6-members aromatic ring, containing 1 to 4 heteroatoms chosen from N, O and S, optionally substituted;Rd represents a linear, branched or cyclic (C1-C6) alkyl, optionally substituted by 1 to 4 halogens;or R1 represents Rc or CHReRc or CHReRd;Re represents H, OH, NH2, NH—(C1-C6)-alk or N-(C1-C6)-alk2, or NH—(C1-C7)-acyl or NHRc;R2 represents H, (CH2)m—NRaRb, Rc, CHReRc or CHReRd, and R′2 represents H; it being understood that R1 and R2 cannot at the same time be H or that R1 and R2 or R2 and R1 cannot be one (CH2)m—NRaRb or Rc or H and the other one OH, or one H and the other one NH2, or one H and the other one (CH2)m—NRaRb in which Ra and Rb represent H or alkyl or C(O)Rd, in which Rd represents an unsubstituted alkyl or cycloalkyl; or R1 has the above definition except H and R2 and R′2 together represent gem dialkyl or alkyl-oxime, or R2 and R′2 represent respectively Rc or Rd and OH, NH2, NHRc or NHRf, Rf being a (C1-C7) acyl radical;or R1 represents H and R2 and R′2 together represent alkyl-oxime or one represents Rc and the other one represents OH, NH2, NHRc or NHRf;n is 0 or 1;R3 and R′3 represent H or (C1-C6) alkyl optionally substituted by 1 to 3 halogens or R3 represents (C1-C6) alkoxy carbonyl and R′3 represents H;R4 represents methyl optionally substituted by halogen;R5 represents H, (C1-C6) alkyl or (C7-C12) arylalkyl;R6 represents H, fluorine, NO2, CF3 or CN;in the form of enantiomers or mixtures, as well as their salts with acids and bases; their preparation and their application as anti-bacterials, in both human and veterinary medicine.

4-Aminothiourea prolinol tert-butyldiphenylsilyl ether: A chiral secondary amine-thiourea as organocatalyst for enantioselective anti-mannich reactions

anti-Selective Mannich reactions of N-p-methoxyphenyl (PMP)-protected α-iminoglyoxylate with unmodified aldehydes or ketones were effectively catalyzed by 4-aminothiourea prolinol tert-butyldiphenylsilyl ether. The reactions led to chiral β-amino carbonyl compounds in high yields (up to 94%), excellent diastereo- and enantioselectivities (up to 98% de and >99% ee). The study demonstrated for the first time that direct Mannich-type reactions of unmodified aldehydes or ketones to aiminoglyoxylate can be promoted by secondary amine-thiourea chiral organocatalyst.

A convenient, high-yield synthesis of 1-substituted uracil and thymine derivatives

Novel reagents for the synthesis of 1-substituted uracil and thymine derivatives have been developed. The aminolysis of 2- or 4-nitrophenyl 3-ethoxyacryloylcarbamate and 3-ethoxy-2-methylacryloylcarbamate with a variety of primary amino derivatives procee

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.