101469-92-5

Basic information

• Product Name: N-(tert-Butoxycarbonyl)-(S)-(+)-3-pyrrolidinol
• Synonyms: BOC-(S)-3-HYDROXYPYRROLIDINE;(3S)-(+)-N-BOC-3-HYDROXYPYRROLIDINE;1-PYRROLIDINECARBOXYLIC ACID, 3-HYDROXY-, 1,1-DIMETHYLETHYL ESTER, (3S)-;(S)-(+)-N-(TERT-BUTOXYCARBONYL)-3-HYDROXYPYRROLIDINE;(S)-N-(TERT-BUTOXYCARBONYL)-3-HYDROXYPYRROLIDINE;(S)-N-BOC-3-PYRROLIDINOL;(S)-N-BOC-3-HYDROXYPYRROLIDINE HYDROCHLORIDE;(S)-TERT-BUTYL 3-HYDROXYPYRROLIDINE-1-CARBOXYLATE
• CAS NO: 101469-92-5
• Molecular Formula: C₉H₁₇NO₃
• Molecular Weight: 187.24
• EINECS: 1592732-453-0
• Product Categories: pharmacetical;Pyrrole&Pyrrolidine&Pyrroline;Benzenes;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral chemicals
• Mol File: 101469-92-5.mol

Chemical Properties

• Melting Point: 60-64 °C(lit.)
• Boiling Point: 273.3 °C at 760 mmHg
• Flash Point: 119.1 °C
• Appearance: White to pale yellow/Crystalline Powder
• Density: 1.142 g/cm³
• Vapor Pressure: 0.000742mmHg at 25°C
• Refractive Index: 27 ° (C=1, MeOH)
• Storage Temp.: Store at 0-5°C
• Solubility: soluble in Methanol
• PKA: 14.74±0.20(Predicted)
• BRN: 6271108
• CAS DataBase Reference: N-(tert-Butoxycarbonyl)-(S)-(+)-3-pyrrolidinol(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-Butoxycarbonyl)-(S)-(+)-3-pyrrolidinol(101469-92-5)
• EPA Substance Registry System: N-(tert-Butoxycarbonyl)-(S)-(+)-3-pyrrolidinol(101469-92-5)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25-37/38-41-R41-R37/38-R25
• Safety Statements: 26-39-45-S45-S39-S26
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• F: 10
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 101469-92-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
N-(tert-Butoxycarbonyl)-(S)-(+)-3-pyrrolidinol is used as a key reactant for the synthesis of several pharmaceutical compounds, including:
1. tert-Butyl 3-(2-bromophenoxy)pyrrolidine-1-carboxylate, which serves as a crucial intermediate in the preparation of IkB-kinase IKK2 inhibitors. These inhibitors play a significant role in the regulation of various cellular processes, including inflammation and immune responses.
2. Dimethoxy-pyrrolidylquinazoline, a compound with potential applications in the development of novel therapeutic agents targeting various diseases.
3. Peptidomimetic quinoline derivatives, which are essential in the design of new drugs with improved bioavailability, selectivity, and potency.
Used in Chemical Research:
In addition to its applications in the pharmaceutical industry, N-(tert-Butoxycarbonyl)-(S)-(+)-3-pyrrolidinol is also utilized in chemical research for the development of new synthetic methods, the study of reaction mechanisms, and the exploration of novel chemical transformations.
Used in Drug Delivery Systems:
Similar to gallotannin, N-(tert-Butoxycarbonyl)-(S)-(+)-3-pyrrolidinol can be incorporated into drug delivery systems to enhance the bioavailability, targeting, and therapeutic efficacy of various pharmaceutical compounds. This application can lead to the development of more effective treatments for a wide range of diseases and conditions.

InChI:InChI=1/C9H17NO3/c1-9(2,3)13-8(12)10-5-4-7(11)6-10/h7,11H,4-6H2,1-3H3/t7-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 101469-91-4 (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 100243-39-8 3-hydroxypyrrolidine 
• 101385-90-4 (S)-N-benzyl-3-hydroxypyrrolidine 
• 216062-06-5 (1'R,3S)-1-tert-butyloxycarbonyl-3-(1',2'-diphenylethoxy)pyrrolidine 
• 132945-74-5 (S)-N-tert-butoxycarbonylpyrrolidin-3-yl benzoate 
• 109431-87-0 (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate 
• 584-08-7 potassium carbonate 
• 101385-91-5 (S)-tert-butyl 3-acetoxypyrrolidine-1-carboxylate 
• 122536-94-1 (S)-3-hydroxypyrrolidine hydrochloride 
• 101385-93-7 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 847942-82-9 (3S)-N-(tert-butyloxycarbonyl)-3-(benzyloxy)pyrrolidine 
• 330797-85-8 (R)-3-(5-bromo-pyridin-3-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 150610-40-5 tert-butyl (3R)-3-[4-(2-ethoxy-2-oxoacetyl)phenoxy]-1-pyrrolidinecarboxylate 
• 1224514-70-8 (R)-3-(pyridin-2-yloxy)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 960491-88-7 tert-butyl (3R)-3-[2-(trifluoromethyl)phenoxy]-pyrrolidine-1-carboxylate 
• 1264038-41-6 (R)-3-(5-chloropyrimidin-2-yloxy)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 109431-87-0 (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate 
• 127423-61-4 tert-butyl (3R)-3-methylsulfonyloxypyrrolidine-1-carboxylate 
• 101408-94-0 3R-acetoxypyrrolidine-1-carboxylic acid tert-butyl ester 
• 132945-74-5 (S)-N-tert-butoxycarbonylpyrrolidin-3-yl benzoate 
• 876617-25-3 (R)-1-N-tert-butoxycarbonyl-3-fluoropyrrolidine 

Relevant articles and documents

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.

Selection of microbial biocatalysts for the reduction of cyclic and heterocyclic ketones

The reduction of carbonyl compounds plays an important role in the synthesis of complex chiral molecules. In particular, enantiopure substituted cyclic and heterocyclic compounds are useful intermediates for the synthesis of several antiviral, antitumor, and antibiotic agents, and recently, they have also been used as organocatalysts for C-C addition. Alcohol dehydrogenases (ADH) are enzymes involved in the transformation of prochiral ketones to chiral hydroxyl compounds. While significant scientific effort has been paid to the use of aliphatic and exocyclic ketones as ADH substrates, reports on (hetero)cyclic carbonyl compounds as substrates of these enzymes are scarce. In the present study, 109 bacteria and 36 fungi were screened, resulting in 10 organisms belonging to both kingdoms capable of transforming cyclic and heterocyclic ketones into the corresponding alcohols. Among them, Erwinia chrysanthemi could quantitatively reduce cyclododecanone and Geotrichum candidum could stereoselectively reduce N-Boc-3-piperidone and N-Boc-3-pyrrolidinone to their corresponding (S)-alcohols; however, the anti-Prelog isomer was obtained when acetophenone was the substrate.

Enantioselective reduction of heterocyclic ketones with low level of asymmetry using carrots

A whole spectrum of biocatalysts for asymmetric reduction of prochiral ketones is well known including the Daucus carota root. However, this type of reaction is still challenging when pro-chiral ketones present low level of asymmetry, like heterocyclic ketones. In this work, 4,5-dihydro-3(2H)-thiophenone (1), 2-methyltetrahydrofuran-3-one (2), N-Boc-3-pyrrolidinone (3), 1-Z-3-pyrrolidinone (4) and 1-benzyl-3-pyrrolidinone (5) were studied in order to obtain the respective enantioselective heterocyclic secondary alcohols. Except for 5, the corresponding alcohols were obtained in high values of conversion and with high selectivity. In order to circumvent the low isolated yield of the corresponding chiral alcohol from 2, we observed that the use of carrots in the absence of water is feasible. Addition of co-solvents was needed to the water-insoluble ketones 3 and 4. Comparatively, baker’s yeast was used for bio reductions of 1, 3 and 4. And in terms of conversion, selectivity and work-up, the use of carrots were a more efficient biocatalyst, as well as a viable method for obtaining 5-member heterocyclic secondary alcohols.

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