132482-06-5

Basic information

• Product Name: tert-butyl (2R)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylate
• Synonyms: (R)-tert-Butyl 2-(2-hydroxyethyl)pyrrolidine-1-carboxylate;(R)-1-Boc-2-(2-hydroxyethyl)pyrrolidine;tert-butyl (2R)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylate
• CAS NO: 132482-06-5
• Molecular Formula: C₁₁H₂₁NO₃
• Molecular Weight: 215.29
• Mol File: 132482-06-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: tert-butyl (2R)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (2R)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylate(132482-06-5)
• EPA Substance Registry System: tert-butyl (2R)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylate(132482-06-5)

Safety Data

• Hazardous Substances Data: 132482-06-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Tert-butyl (2R)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylate serves as an intermediate in the synthesis of various pharmaceuticals. Its unique structure allows it to participate in a range of chemical reactions, facilitating the development of new drug candidates with potential therapeutic applications.
Used in Organic Compounds Synthesis:
In the realm of organic chemistry, tert-butyl (2R)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylate is utilized for the synthesis of diverse organic compounds. Its reactivity and functional groups make it a suitable building block for creating complex organic molecules with specific properties and functions.
Used in Chemical Research:
tert-butyl (2R)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylate's potential biological activity and its ability to engage in various chemical reactions also make it a valuable tool in chemical research. It can be used to study reaction mechanisms, explore new synthetic routes, and investigate the properties of novel chemical entities.

Upstream product

• 75-21-8 oxirane 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 152665-79-7 (R)-tert-butyl 2-(2-diazoacetyl)pyrrolidine-1-carboxylate 
• 344-25-2 D-Prolin 
• 24424-99-5 di-tert-butyl dicarbonate 
• 646062-88-6 (E)-(6-tert-butoxycarbonylamino)-2-hexenal 
• 101555-60-6 2-(R)-carboxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 
• 340129-94-4 (R)-1-[(1,1-dimethylethoxy)carbonyl]-2-ethenylpyrrolidine 
• 59378-81-3 1-(tert-butoxycarbonyl)prolin-2R-ol 
• 59378-82-4 N-(tert-butoxycarbonyl)pyrrolidine-2-carboxaldehyde 
• 132482-05-4 methyl (R)-2-[N(1')-(tert-butoxycarbonyl)pyrrolidin-2'-yl]ethanoate 

Downstream Products

• 201038-72-4 (R)-1-(2-(1-(3-benzyloxy-benzenesuylfonyl)-pyrrolidin-2-yl)-ethyl)-4-methyl piperidine 
• 261901-57-9 SB 269970 A 
• 1433607-60-3 (E)-2-amino-7-(4-fluoro-2-(pyridin-3-yl)phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one O-(R)-(2-(pyrrolidin-2-yl)ethyl)oxime 
• 1433607-76-1 (2R)-N-Boc-2-(((2-((E)-2-amino-7-(4-fluoro-2-(pyridin-3-yl)phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-ylidene)amino)oxy)ethyl)pyrrolidine 

Relevant articles and documents

Boron trifluoride etherate-assisted ring opening of ethylene oxide by a chiral organolithium: Enantioselective synthesis of (R)-N-Boc-2-(2-hydroxyethyl) pyrrolidine

A practical synthesis of (R)-N-Boc-2-(2-hydroxyethyl)pyrrolidine in high enantiomeric purity is described. The synthesis involves BF3· Et2O-assisted ring opening of ethylene oxide by a homochiral carbanion (R)-3, which is derived from sparteine-mediated asymmetric deprotonative lithiation of 1-Boc-pyrrolidine.

Tetrahydropyrido [3, 4-d] pyrimidine derivative and medical application thereof

The invention relates to a compound as shown in a general formula (I) or a stereoisomer, a deuterated compound, a solvate, a prodrug, a metabolite, a pharmaceutically acceptable salt or eutectic crystal thereof, an intermediate and a preparation method thereof, and application of the compound in preparation of drugs for treating diseases related to KRas-G12C activity or expression quantity.

Novel multi-target azinesulfonamides of cyclic amine derivatives as potential antipsychotics with pro-social and pro-cognitive effects

Currently used antipsychotics are characterized by multireceptor mode of action. While antagonism of dopamine D2 receptors is responsible for the alleviation of “positive” symptoms of schizophrenia and the effects at other, particularly serotonergic receptors are necessary for their additional therapeutic effects, there is no consensus regarding an “ideal” target engagement. Here, a detailed SAR analysis in a series of 45 novel azinesulfonamides of cyclic amine derivatives, involving the aryl-piperazine/piperidine pharmacophore, central alicyclic amine and azinesulfonamide groups has led to the selection of (S)-4-((2-(2-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)ethyl)pyrrolidin-1-yl)sulfonyl)isoquinoline (62). The polypharmacology profile of 62, characterized by partial 5-HT1AR agonism, 5-HT2A/5-HT7/D2/D3R antagonism, and blockade of SERT, reduced the “positive”-like, and “negative”-like symptoms of psychoses. Compound 62 produced no catalepsy, demonstrated a low hyperprolactinemia liability and displayed pro-cognitive effects in the novel object recognition task and attentional set-shifting test. While association of in vitro features with the promising in vivo profile of 62 is still not fully established, its clinical efficacy should be verified in further stages of development.

(QUINOLINE OR ISOQUINOLINE)SULFONAMIDES OF CYCLIC AMINES AS ANTIPSYCHOTIC DRUGS

The invention relates to compounds of general formula (I) wherein: one of A1 and A2 represents a nitrogen atom and the other a carbon atom optionally substituted by halogen; the wave line between the sulfonamido moiety and B/C rings represents a single bond linking the sulfur atom to a non-bridgehead carbon atom, with the proviso that the part of ring C being detached by the dashed broken line is unsubstituted; n represents an integer from 0 to 3; Y represents a nitrogen or carbon atom; Z represents a 5-6 membered aromatic/ heteroaromatic ring optionally fused with a further aromatic or non- aromatic 5-6 membered heterocycle, the condensed ring system being linked via a non-bridgehead carbon atom. The compounds display high affinity for the D2, D3, 5-HT1A, 5-HT2A- 5-HT6 and 5-HT7 receptors and are useful for the treatment of psychotropic diseases or disorders associated with disturbances of the dopaminergic/ serotoninergic systems such as schizophrenia and autism.

QUINAZOLINE DERIVATIVES WITH HSP90 INHIBITORY ACTIVITY

Compounds of general formula (I): or a stereoisomer, tautomer, polymorph, hydrate, solvate, or a pharmaceutically acceptable salt thereof, wherein R is as defined herein, are useful for the treatment of diseases and conditions which are mediated by excessive or inappropriate Hsp90 activity such as proliferative diseases, e.g. cancers, viral and fungal infections, neurodegenerative or inflammatory diseases or conditions. The invention also relates to the preparation of these compounds as well as to pharmaceutical compositions comprising them.

SUBSTITUTED BENZHYDRYLETHERS

Disclosed herein are substituted benzhydrylethers of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and methods of their use thereof.

Efficient Arndt-Eistert synthesis of selective 5-HT7 receptor antagonist SB-269970

This contribution describes a novel Arndt-Eistert approach for the efficient synthesis of the potent and selective 5-HT7-antagonist, (R)-3-(2-(2-(4-methylpiperidin-1-yl)-ethyl)pyrrolidine-1-sulfonyl)phenol (SB-269970), from D-proline. The synthesis was ca

Enantioselective organocatalytic intramolecular aza-Michael reaction: A concise synthesis of (+)-sedamine, (+)-allosedamine, and (+)-coniine

(Chemical Equation Presented) The intramolecular aza-Michael reaction of carbamates bearing remote α,β-unsaturated aldehydes under organocatalytic conditions took place with good yields and excellent ee's when Jorgensen catalyst IV was used in the process, giving rise to the enantioselective formation of several five- and six-membered heterocycles. The developed methodology was applied to the synthesis of three piperidine alkaloids.

Synthesis by chiral diamine-mediated asymmetric alkylation

Chiral synthesis from an achiral starting material by chiral diamine-mediated, such as sparteine-mediated, intermolecular asymmetric alkylation with a strained cyclic ether in the presence of a Lewis acid.

Total syntheses of the tylophora alkaloids cryptopleurine, (-)-antofine, (-)-tylophorine, and (-)-ficuseptine C

A concise, efficient and modular approach to the tylophora alkaloids is described, a family of potent cytotoxic agents that are equally effective against drug sensitive and multidrug resistant cancer cell lines. The advantages of the chosen route are illustrated by the total syntheses of the phenanthroquinolizidine cryptopleurine (1) and the phenanthroindolizidines (-)-antofine (2), (-)-tylophorine (3), and their only recently isolated congener (-)-ficuseptine C (4). The key steps consist in a Suzuki cross-coupling between a (commercial) boronic acid and a simple aryl-l,2-dihalide followed by elaboration of the resulting products into the corresponding 2-alkynyl-biphenyl derivatives 27, 33, 41 and 46. The latter undergo PtCl2-catalyzed cycloisomerizations with formation of the functionalized phenanthrenes 28, 34, 42 and 47, which were transformed into the targeted alkaloids by a deprotection/Pictet-Spengler annulation tandem. Due to the flexibility and robust character of this approach, it might enable a systematic exploration of the pharmacological profile of this promising class of bioactive natural products.