109431-87-0

Basic information

• Product Name: (R)-(-)-N-Boc-3-pyrrolidinol
• Synonyms: BOC-(R)-3-HYDROXYPYRROLIDINE;(3R)-(-)-N-BOC-3-HYDROXYPYRROLIDINE;1-PYRROLIDINECARBOXYLIC ACID, 3-HYDROXY-, 1,1-DIMETHYLETHYL ESTER, (3R)-;N-TERT-BUTOXYCARBONYL-(R)-(-)-3-PYRROLIDINOL;N-T-BOC-(R)-3-HYDROXYPYRROLIDINE;(R)-3-HYDROXYPYRROLIDINE HYDROCHLORIDE-N-BOC;(R)-3-HYDROXYPYRROLIDINE, N-TERT-BUTOXYCARBONYL;(R)-1-BOC-3-PYRROLIDINOL
• CAS NO: 109431-87-0
• Molecular Formula: C₉H₁₇NO₃
• Molecular Weight: 187.24
• Product Categories: pharmacetical;Benzenes;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral chemicals
• Mol File: 109431-87-0.mol
• Article Data: 59

Chemical Properties

• Melting Point: 62-65 °C(lit.)
• Boiling Point: 273.3 °C at 760 mmHg
• Flash Point: 119.1 °C
• Appearance: White to off-white/Powder
• Density: 1.142 g/cm³
• Refractive Index: -27 ° (C=1, MeOH)
• Storage Temp.: Store at 0-5°C
• Solubility: soluble in Methanol
• PKA: 14.74±0.20(Predicted)
• CAS DataBase Reference: (R)-(-)-N-Boc-3-pyrrolidinol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-N-Boc-3-pyrrolidinol(109431-87-0)
• EPA Substance Registry System: (R)-(-)-N-Boc-3-pyrrolidinol(109431-87-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-53-50-50/53
• Safety Statements: 26-36
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 109431-87-0(Hazardous Substances Data)

Usage

Description

(R)-(-)-N-Boc-3-pyrrolidinol, also known as (R)-3-(tert-butoxycarbonylamino)pyrrolidin-1-ol, is a chiral amine compound with a molecular formula of C9H17NO2. It is a white to off-white powder and is an important building block in organic synthesis, particularly in the preparation of pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
(R)-(-)-N-Boc-3-pyrrolidinol is used as a key intermediate in the synthesis of various pharmaceuticals, including antibiotics, antidepressants, and antipsychotics. Its chiral nature allows for the selective synthesis of enantiomerically pure compounds, which is crucial for the development of drugs with improved efficacy and reduced side effects.
Used in Agrochemical Industry:
(R)-(-)-N-Boc-3-pyrrolidinol is also used as a precursor in the synthesis of agrochemicals, such as insecticides and herbicides. Its ability to form stable derivatives with other molecules makes it a valuable component in the development of new and effective crop protection agents.
Used in Synthesis of Ligands for the Nicotinic Acetylcholine Receptor:
(R)-(-)-N-Boc-3-pyrrolidinol is used as a building block in the synthesis of ligands for the nicotinic acetylcholine receptor. These ligands are important for the study of the receptor's function and for the development of drugs targeting this receptor, which is involved in various neurological disorders, such as Alzheimer's disease and schizophrenia.
Chemical Properties:
(R)-(-)-N-Boc-3-pyrrolidinol is a white to off-white powder with a molecular weight of 173.24 g/mol. It is soluble in common organic solvents, such as dichloromethane, ethyl acetate, and acetone, and has a melting point of around 65-68°C. Its chemical stability and reactivity make it a versatile compound for various synthetic applications.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 101469-91-4 (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 40499-83-0 (3R)-pyrrolidinol 
• 101385-90-4 (R)-N-benzyl-3-hydroxypyrrolidine 
• 101385-93-7 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 101408-94-0 3R-acetoxypyrrolidine-1-carboxylic acid tert-butyl ester 
• 132945-75-6 (S)-tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate 
• 101469-92-5 (S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 104706-47-0 (R)-3-hydroxypyrrolidine hydrochloride 
• 51-35-4 4R-4-hydroxyproline 
• 549532-09-4 3R-(tert-butyl-dimethylsilyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 123-91-1 1,4-dioxane 

Downstream Products

• 114676-93-6 (2R,4R)-tert-butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate 
• 114676-61-8 tert-butyl (2S,4R)-4-hydroxyl-2-methylpyrrolidine-1-carboxylate 
• 1061749-09-4 (S)-3-{3-[6-acetylamino-2-(3,5-dimethyl-pyrazol-1-yl)-pyrimidin-4-yl]-5-fluoro-phenoxy}-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1092366-92-1 tert-butyl (3R)-3-{[(2-nitrophenyl)sulfonyl]oxy}pyrrolidine-1-carboxylate 
• 1039631-74-7 N-(tert-butoxycarbonyl)-3-(S)-(1-(R)-phenyl-2-N'-pyrrolidinylethyl)aminopyrrolidine 
• 1039631-78-1 N-(tert-butoxycarbonyl)-3-(S)-(1-(R)-phenyl-2-N'-piperidinylethyl)aminopyrrolidine 
• 1039631-76-9 N-(tert-butoxycarbonyl)-3-(S)-(1-(S)-phenyl-2-N'-piperidinylethyl)aminopyrrolidine 
• 1018966-19-2 3-[(4-{[(3S)-1-methylpyrrolidin-3-yl]oxy}phenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide 
• 177947-67-0 (3R)-N-(tert-butyloxycarbonyl)-3-(benzyloxy)pyrrolidine 
• 1029360-55-1 tert-butyl (3S)-3-(2-fluorophenoxy)azolan-1-carboxylate 
• 927892-96-4 (R)-tert-butyl 3-({4-[4-[(4-fluorobenzyl)oxy]-2-oxopyridin-1(2H)-yl]benzyl}oxy)pyrrolidine-1-carboxylate 
• 518063-52-0 tert-butyl 3-fluoropyrrolidine-1-carboxylate 
• 849106-95-2 (R)-3-(4-chloro-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 942195-01-9 tert-butyl (R)-3-(4-iodophenoxy)pyrrolidine-1-carboxylate 

Relevant articles and documents

Enantiospecific Synthesis of the (4R)-1-Azabicycloheptane Ring System

An enantioselective synthesis of (4R)-1-azabicycloheptane derivatives is described commencing from readily available trans-4-hydroxy-L-proline which is converted into the key intermediate (3R)-N-(tert-butoxycarbonyl)-3-methylsulfonyloxypyrrolidine 4.Reaction of the sulfonate ester 4 with an enolate anion yields a mixtute of (3R)-pyrrolidineacetic esters 8 and 9 which are reduced to the corresponding alcohols 10 and 11.Conversion of the alcohols into the sulfonate esters 12 and 13 followed by deprotection of the pyrrolidine nitrogen leads to cyclisation yielding the (4R)-1-azabicycloheptane derivatives 14 and 15.

NOVEL OXADIAZOLES

The present invention relates to novel compound of Formula I, wherein, R1, A1, A2, A3, A4, A5, L1, A, L2 and R2 are as defined in the detailed description. The present invention also relates to a combination or a composition comprising the compound of Formula I.

Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles

The first asymmetric cooperative Lewis base/palladium catalyzed benzylic alkylation of acyclic esters is reported. This reaction proceeds via stereodefined C1-ammonium enolate nucleophiles. Critical to its success was the identification of benzylic phosphate electrophiles, which were uniquely reactive. Alkylated products were obtained with very high levels of enantioselectivity, and this method has been applied toward the synthesis of the thrombin inhibitor DX-9065a.