338945-22-5

Usage

Uses

Used in Organic Synthesis:
(S)-2-IodoMethyl-pyrrolidine-1-carboxylic acid tert-butyl ester is used as a key intermediate for the synthesis of various bioactive molecules. Its unique structure and functional groups allow for further chemical modifications, making it a versatile component in creating a wide range of compounds with potential applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (S)-2-IodoMethyl-pyrrolidine-1-carboxylic acid tert-butyl ester is used as a starting material for the development of pharmaceutical drugs. Its chiral nature and chemical properties make it an attractive candidate for designing and synthesizing novel drug molecules with improved efficacy and selectivity.
Used in Pharmaceutical Drug Development:
(S)-2-IodoMethyl-pyrrolidine-1-carboxylic acid tert-butyl ester is utilized as a crucial building block in the creation of new pharmaceutical compounds. Its potential applications in this industry stem from its ability to be incorporated into various drug molecules, contributing to the development of innovative treatments for a range of medical conditions.
Used in Chiral Compound Research:
(S)-2-IodoMethyl-pyrrolidine-1-carboxylic acid tert-butyl ester is also used in the study of chiral compounds, which are essential in understanding the differences in biological activity and pharmacological effects between enantiomers. This research can lead to the development of more effective and safer drugs by exploiting the unique properties of chiral molecules.

Upstream product

• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 1972-28-7 diethylazodicarboxylate 
• 86661-32-7 (S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate 
• 147-85-3 L-proline 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 144-55-8 sodium hydrogencarbonate 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 132482-09-8 tert-butyl (2S)-2-{[(methylsulfonyl)oxy]methyl}-pyrrolidine-1-carboxylate 
• 1004993-43-4 tert-butyl (2S)-2-[(phenylselenonyl)methyl]pyrrolidine-1-carboxylate 

Downstream Products

• 1318240-22-0 (S)-tert-butyl 2-(2-tolylmethyl)pyrrolidine-1-carboxylate 
• 1243726-25-1 (S)-tert-butyl 2-(2-naphthylmethyl)pyrrolidine-1-carboxylate 
• 1257204-48-0 (S)-(+)-tert-butyl 2-(3-methoxybenzyl)pyrrolidine-1-carboxylate 
• 1194030-94-8 (S )-(+)-tert-butyl 2-benzylpyrrolidine-1-carboxylate 
• 202925-92-6 N-Pent-4-enylcarbamic acid tert-butyl ester 
• 1232829-58-1 (S)-tert-butyl 2-(4-fluorophenylmethyl)pyrrolidine-1-carboxylate 
• 1318240-23-1 (S)-tert-butyl 2-(3,5-dimethoxyphenylmethyl)pyrrolidine-1-carboxylate 
• 1315563-38-2 C₁₇H₂₅NO₃S 
• 168049-26-1 tert-butyl (2S)-2-(azidomethyl)-1-pyrrolidinecarboxylate 
• 1257204-50-4 (S )-(-)-tert-butyl 2-(4-aminobenzyl)pyrrolidine-1-carboxylate 
• 1257204-52-6 (S )-(+)-tert-butyl 2-(3,4-dimethoxybenzyl)pyrrolidine-1-carboxylate 
• 1257204-51-5 (S )-(+)-tert-butyl 2-(4-(methoxycarbonyl)benzyl)pyrrolidine-1-carboxylate 
• 1232830-21-5 (S )-(-)-tert-butyl 2-(3-(trifluoromethyl)benzyl)pyrrolidine-1-carboxylate 
• 1257984-85-2 (S )-(+)-tert-butyl 2-(4-methoxybenzyl)pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

A Bifunctional B,N-Based Asymmetric Catalytic Nitrostyrene-Michael Addition Acting through a 10-Membered Ring Cyclic Transition State

The B,N-bifunctional catalyst homoboroproline has been applied to a catalytic asymmetric nitroalkene-Michael addition to β-nitrostyrene analogues, showing broad substrate tolerance, high conversions and moderate to good asymmetric induction. The ability o

Staudinger/aza-Wittig reaction to access Nβ-protected amino alkyl isothiocyanates

A unified approach to access Nβ-protected amino alkyl isothiocyanates using Nβ-protected amino alkyl azides through a general strategy of Staudinger/aza-Wittig reaction is described. The type of protocol used to access isothiocyanates depends on the availability of precursors and also, especially in the amino acid chemistry, on the behavior of other labile groups towards the reagents used in the protocols; fortunately, we were not concerned about both these factors as precursor-azides were prepared easily by standard protocols, and the present protocol can pave the way for accessing title compounds without affecting Boc, Cbz and Fmoc protecting groups, and benzyl and tertiary butyl groups in the side chains. The present strategy eliminates the need for the use of amines to obtain title compounds and thus, this method is step-economical; additional advantages include retention of chirality, convenient handling and easy purification. A few hitherto unreported compounds were also prepared, and all final compounds were completely characterized by IR, mass, optical rotation, and 1H and 13C NMR studies.

Sequential deprotectionecyclisation reaction: Stereoselective synthesis of azabicyclic β-enamino ester derivatives and (-) indolizidine 209D

This paper describes a new strategy for the stereoselective synthesis of pyrrolizidine and indolizidine based enamino esters and their acyl derivatives from L-proline. The key reaction in this process involves deprotection followed by ring closure of cyclic N-Boc amino-β-ketoesters. Also, the synthesis of 5R,9R- (-)-indolizidine 209D has been accomplished using this protocol.

Enantioselective synthesis of (R)-homoboroproline from (S)-proline using a borylation approach

(S)-Proline was converted through a five-step sequence into (R)-homoboroproline hydrochloride in 29% overall yield with 97% The key step was the conversion of N-Boc iodomethylpyrrolidine into the corresponding pinacol boronate ester by an efficient copper(I)-catalyzed borylation reaction by using bispinacolatodiboron.

Cobalt-catalyzed carbon-carbon bond formation: Synthesis and applications of enantiopure pyrrolidine derivatives[1]

In the presence of cobalt catalysts and tetramethylethylenediamine (TMEDA), the iodine atom in (S)-2-(iodomethyl)pyrrolidines was replaced by an aryl or an alkynyl group from the corresponding Grignard reagent, and the coupling products were obtained in good to excellent yields (16 examples; 75-94% yields). The scope and limitations of this protocol were examined. The stereochemistry of the pyrrolidines was unaffected by the reaction conditions. The coupling products are important building blocks of phenanthroindolizidine alkaloids. Palladium-catalyzed formal [4+2] cycloaddition of 2,2′-diiodobiphenyl with the thus-generated (S)-2-(3-trimethylsilyl-2-propynyl)pyrrolidine gave a good yield of the desilylated phenanthrene, which was then converted into unnatural (+)-(S)-tylophorine by the Pictet-Spengler cyclization. Copyright

The diastereoselective alkylation of arenesulfenate anions using homochiral electrophiles

A series of Boc-protected β-amino sulfoxides were prepared by the reaction of arenesulfenate anions with chiral Boc-protected β-amino iodides. The stereoselective substitution reaction is believed to arise through precoordination of the sulfenate counteri

In situ trapping of Boc-2-pyrrolidinylmethylzinc iodide with aryl iodides: Direct synthesis of 2-benzylpyrrolidines

Addition of (S)-(+)-tert-butyl 2-(iodomethyl)pyrrolidine-1-carboxylate to activated zinc, aryl halides, and a catalyst derived from Pd2(dba) 3 (2.5 mol %) and SPhos (5 mol %) in DMF allows trapping of the corresponding organozinc rea

Substituted Disulfonamide Compounds

Substituted disulfonamide compounds corresponding to formula I: In which R1, R2, R3, R4a, R4b, R5a, R5b, R8, R9a, R9b, R10, R11, a, b, s, t and A have defined meanings, pharmaceutical compositions containing one or more such compounds, processes for preparing such compounds, and a method of using such compounds for the treatment or inhibition of pain and/or other conditions mediated by the bradykinin receptor 1 (BR1).

Selenium promoted synthesis of enantiopure pyrrolidines starting from chiral aminoalcohols

Starting from commercially available enantiomerically pure aminoalcohols and using simple conversions promoted by organoselenium reagents, several enantiomerically pure substituted pyrrolidines were prepared. After double protections (R)- or (S)-2-phenylg

An efficient and convergent synthesis of the potent and selective H3 antagonist ABT-239

An efficient and convergent process for the preparation of a potent and selective H3 receptor antagonist, ABT-239, 1A was accomplished with an overall yield of 64%. The key step in the synthesis is a Sonogashira coupling/cyclization reaction of 1-but-3-ynyl-2-(R)-methylpyrrolidine (9) with 4′-hydroxy-3′-iodo-biphenyl-4-carbonitrile (3). Additionally, the key amine component 2-(R)-methylpyrrolidine (7) was effectively synthesized from the readily available Boc-l-prolinol with a simple catalytical hydrogenolysis as the key step. This column chromatography-free process is highlighted by several simple work-up and purification procedures and is amendable to the large-scale preparation of 1A.