132945-74-5

Basic information

• Product Name: (S)-N-tert-butoxycarbonylpyrrolidin-3-yl benzoate
• Synonyms: (S)-N-tert-butoxycarbonylpyrrolidin-3-yl benzoate
• CAS NO: 132945-74-5
• Molecular Weight: 291.347
• Mol File: 132945-74-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 387.3±35.0 °C(Predicted)
• Density: 1.16±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (S)-N-tert-butoxycarbonylpyrrolidin-3-yl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-tert-butoxycarbonylpyrrolidin-3-yl benzoate(132945-74-5)
• EPA Substance Registry System: (S)-N-tert-butoxycarbonylpyrrolidin-3-yl benzoate(132945-74-5)

Safety Data

• Hazardous Substances Data: 132945-74-5(Hazardous Substances Data)

Upstream product

• 109431-87-0 (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate 
• 65-85-0 benzoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 127423-61-4 tert-butyl (3R)-3-methylsulfonyloxypyrrolidine-1-carboxylate 
• 98-88-4 benzoyl chloride 
• 101469-92-5 (S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 259184-49-1 (S)-3-benzoyloxypyrrolidine 
• 101469-92-5 (S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Preparation method of (S)-3-hydroxypyrrolidine hydrochloride

The invention relates to the field of chemistry, particularly a preparation method of a key intermediate (S)-3-hydroxypyrrolidine hydrochloride of darifenacin for treating overactive bladder syndrome and an antihypertensive drug barnidipine. The preparation method comprises the following steps: carrying out Mitsunobu reaction on (R)-1-N-tert-butyloxycarbonyl-3-hydroxypyrrolidine so as to be condensed with acid to obtain an upturned-structure ester, hydrolyzing ester bond under alkaline conditions to obtain (S)-1-N-tert-butyloxycarbonyl-3-hydroxypyrrolidine, and removing Boc protecting groups under acidic conditions, thereby finally obtaining the key intermediate. The method is simple and easy to implement, has the advantages of cheap and accessible raw materials, lower cost and high yield, and has potential production value.

Synthesis of piperidinyl and pyrrolidinyl butyrates for potential in vivo measurement of cerebral butyrylcholinesterase activity

Biochemical changes in postmortem brains of Alzheimer's disease patients include decreased acetylcholinesterase and choline acetyl transferase activity, indicating reduced activity of the central cholinergic system, while butyrylcholinesterase (BChE) activity increases. A method that can measure regional BChE activity in the brain in vivo may be useful for investigating the relationship between BChE and Alzheimer's disease. Seven compounds, either piperidinyl or pyrrolidinyl butyrates, were synthesized as BChE substrate radiotracers to map central BChE activity in vivo by positron emission tomography (PET). 14C-labeled compounds were assayed to determine their hydrolysis rates by BChE and the partition coefficient. The five esters of secondary alcohols had lipophilic properties sufficient to pass readily through the blood-brain barrier while the metabolites were sufficiently hydrophilic to be retained in the brain. The esters showed moderate hydrolysis rates by BChE and high specificity for BChE relative to acetylcholinesterase, while two esters of primary alcohols were hydrolyzed too rapidly to estimate reliably the local cerebral BChE activity. From these results, we conclude that one or more of these five esters, when labeled with 11C, would be a useful tracer for quantification of BChE activity by PET.