152665-75-3

Basic information

• Product Name: (S)-tert-butyl 2-(2-broMoacetyl)pyrrolidine-1-carboxylate
• Synonyms: (S)-tert-butyl 2-(2-broMoacetyl)pyrrolidine-1-carboxylate
• CAS NO: 152665-75-3
• Molecular Formula: C₁₁H₁₈BrNO₃
• Molecular Weight: 292.16952
• Mol File: 152665-75-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-tert-butyl 2-(2-broMoacetyl)pyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-tert-butyl 2-(2-broMoacetyl)pyrrolidine-1-carboxylate(152665-75-3)
• EPA Substance Registry System: (S)-tert-butyl 2-(2-broMoacetyl)pyrrolidine-1-carboxylate(152665-75-3)

Safety Data

• Hazardous Substances Data: 152665-75-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-tert-butyl 2-(2-bromoacetyl)pyrrolidine-1-carboxylate is used as a building block in organic synthesis for the preparation of various drug molecules and bioactive compounds. Its unique structure allows for the creation of a wide range of molecules with potential therapeutic applications.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (S)-tert-butyl 2-(2-bromoacetyl)pyrrolidine-1-carboxylate is used as a starting material for the synthesis of chiral pyrrolidine-based compounds and pharmaceutical intermediates. Its versatility in synthesis makes it a valuable tool for developing new drugs and improving existing ones.
Used in Medicinal Chemistry:
(S)-tert-butyl 2-(2-bromoacetyl)pyrrolidine-1-carboxylate is also utilized in medicinal chemistry for its potential applications in creating compounds with biological activity. Its structural features enable the development of molecules that can interact with specific biological targets, potentially leading to the discovery of new treatments for various diseases and conditions.

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 101130-03-4 tert-butyl (S)-2-(diazoacetyl)pyrrolidine-1-carboxylate 

Downstream Products

• 1132649-76-3 C₂₅H₃₂N₂O₃ 
• 1338385-04-8 (2R,2'S)-2-(1'-methyl-2'-pyrrolidinyl)-7-phenyl-1,4-benzodioxane 
• 1338385-05-9 (2S,2'S)-2-(1'-methyl-2'-pyrrolidinyl)-7-phenyl-1,4-benzodioxane 
• 1340570-80-0 1-(1'-Boc-2'-pyrrolidinyl)-2-(o-benzyloxy-p-hydroxymethylphenoxy)ethanol 
• 1338384-57-8 (1R,2'S)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o-benzyloxy-p-phenylphenoxy)ethanol 
• 1338384-58-9 (1S,2'S)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o-benzyloxy-p-phenylphenoxy)ethanol 
• 1338384-61-4 (1R,2'S)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o,p-dibenzyloxyphenoxy)ethanol 
• 1338384-62-5 (1S,2'S)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o,p-dibenzyloxyphenoxy)ethanol 
• 1338384-63-6 (1R,2'S)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o-hydroxy-p-methylphenoxy)ethanol 
• 1338384-64-7 (1S,2'S)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o-hydroxy-p-methylphenoxy)ethanol 
• 1338384-67-0 1-(1'-Boc-2'-pyrrolidinyl)-2-(o-hydroxy-p-hydroxymethylphenoxy)ethanol 
• 1338384-68-1 (1R,2'S)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o-hydroxy-p-trityloxymethylphenoxy)ethanol 
• 1338384-69-2 (1S,2'S)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o-hydroxy-p-trityloxymethylphenoxy)ethanol 
• 1338384-71-6 (2S,2'S)-2-(1'-Boc-2'-pyrrolidinyl)-7-trityloxy-1,4-benzodioxane 

Relevant articles and documents

From Oxadiazole to Triazole Analogues: Optimization toward a Dual Orexin Receptor Antagonist with Improved in vivo Efficacy in Dogs

The orexin system is responsible for regulating the sleep-wake cycle. Suvorexant, a dual orexin receptor antagonist (DORA) is approved by the FDA for the treatment of insomnia disorders. Herein, we report the optimization efforts toward a DORA, where our starting point was (5-methoxy-4-methyl-2-[1,2,3]triazol-2-yl-phenyl)-{(S)-2-[5-(2-trifluoromethoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-pyrrolidin-1-yl}methanone (6), a compound which emerged from our in-house research program. Compound 6 was shown to be a potent, brain-penetrating DORA with in vivo efficacy similar to suvorexant in rats. However, shortcomings from low metabolic stability, high plasma protein binding (PPB), low brain free fraction (fu brain), and low aqueous solubility, were identified and hence, compound 6 was not an ideal candidate for further development. Our optimization efforts addressing the above-mentioned shortcomings resulted in the identification of (4-chloro-2-[1,2,3]triazol-2-yl-phenyl)-{(S)-2-methyl-2-[5-(2-trifluoromethoxy-phenyl)-4H-[1,2,4]triazol-3-yl]-pyrrolidin-1-yl}l-methanone (42), a DORA with improved in vivo efficacy compared to 6.

CuI-promoted one-pot synthesis of N-boc protected β-ketotriazole amino acids: Application in the synthesis of new class of dipeptidomimetics

One-pot click chemistry of Nα-Boc-bromomethylketones, NaN3 and propiolic acid affords N-Boc protected 1,4- disubstituted 1,2,3-β-ketotriazole acids in good to excellent yield. The use of CuI as catalyst and DMSO as solvent leads the click react

5-(2-Pyrrolidinyl)oxazolidinones and 2-(2-pyrrolidinyl)benzodioxanes: Synthesis of all the stereoisomers and α4β2 nicotinic affinity

The four stereoisomers of 2-oxazolidinone 5-substituted with 1-methyl-2-pyrrolidinyl (1), of 1,4-benzodioxane 2-substituted with the same residue (2) and of the nor-methyl analogue of this latter (2a) were synthesized as candidate nicotinoids. Of the 12 c