84766-91-6

Basic information

• Product Name: N-BOC PRROLIDIN-2-OL
• Synonyms: N-BOC PRROLIDIN-2-OL;tert-butyl 2-hydroxypyrrolidine-1-carboxylate;N-Boc-Pyrrolidin-2-Ol;2-Hydroxy-1-pyrrolidinecarboxylic Acid 1,1-DiMethylethyl Ester
• CAS NO: 84766-91-6
• Molecular Formula: C₉H₁₇NO₃
• Molecular Weight: 187.237
• Mol File: 84766-91-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 273.3±33.0 °C(Predicted)
• Appearance: /
• Density: 1.142±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, DCM
• PKA: 13.92±0.20(Predicted)
• CAS DataBase Reference: N-BOC PRROLIDIN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC PRROLIDIN-2-OL(84766-91-6)
• EPA Substance Registry System: N-BOC PRROLIDIN-2-OL(84766-91-6)

Safety Data

• Hazardous Substances Data: 84766-91-6(Hazardous Substances Data)

Usage

Description

N-BOC PRROLIDIN-2-OL, also known as 2-Hydroxy-1-pyrrolidinecarboxylic Acid 1,1-Dimethylethyl Ester, is an organic compound that serves as an intermediate in the synthesis of various pharmaceutical agents. It is characterized by its unique molecular structure, which includes a pyrrolidine ring and a protected hydroxyl group, making it a versatile building block in organic synthesis.

Uses

Used in Pharmaceutical Industry:
N-BOC PRROLIDIN-2-OL is used as an intermediate in the synthesis of (E)-6-Amino-2-hexenoic Acid (A609990), a compound with anti-collagenase activity. This makes it a valuable component in the development of pharmaceuticals targeting collagenase enzymes, which are implicated in various pathological conditions, including arthritis and tissue degradation.
In the synthesis process, the N-BOC protecting group in N-BOC PRROLIDIN-2-OL is crucial for preventing unwanted side reactions, ensuring the successful formation of the desired (E)-6-Amino-2-hexenoic Acid. Once the synthesis is complete, the protecting group can be removed to reveal the active pharmaceutical agent.
Overall, N-BOC PRROLIDIN-2-OL plays a significant role in the pharmaceutical industry, contributing to the development of novel therapeutic agents with potential applications in treating various diseases and conditions.

Upstream product

• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 16644-98-7 (E)-1-iodohexene 
• 54145-19-6 2-iodohex-1-ene 
• 201230-82-2 carbon monoxide 
• 78888-18-3 N-tert-butoxycarbonylprop-2-en-1-amine 

Downstream Products

• 646062-88-6 (E)-(6-tert-butoxycarbonylamino)-2-hexenal 
• 760968-82-9 {3-[6-benzyloxy-3-formyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester 
• 760968-87-4 {3-[6-benzyloxy-4-hydroxy-3-methylene-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester 
• 760968-88-5 {3-[6-benzyloxy-3-methylene-4-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester 
• 760968-85-2 {3-[6-benzyloxy-3-hydroxymethyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester 
• 760968-86-3 {3-[6-benzyloxy-1a-hydroxymethyl-3-(toluene-4-sulfonyl)-1a,2,3,7b-tetrahydro-1-oxa-3-aza-cyclopropa[a]naphthalen-2-yl]-propyl}-carbamic acid tert-butyl ester 
• 95687-85-7 8-benzoyl-8-azabicyclo<3.2.1>octane 
• 155394-39-1 1-(o-bromobenzoyl)-2-(prop-2-enyl)pyrrolidine 
• 86953-89-1 N-(tert-Butoxycarbonyl)-2-(2-oxopropyl)pyrrolidine 

Relevant articles and documents

On the synthesis of α-amino sulfoxides

A synthetic study on the preparation of N-Boc α-amino sulfoxides has revealed an unexpected instability which is believed to be due to α-elimination of the sulfoxide to give an iminium ion. Full synthetic details are reported on two main synthetic routes: lithiation and sulfinate trapping of N-Boc heterocycles and oxidation of N-Boc α-amino sulfides. Six novel α-amino sulfoxides were successfully prepared and isolated. It is speculated that four other α-amino sulfoxides were synthesised but could not be isolated due to their propensity to α-eliminate the sulfoxide. Ultimately, a stable, cyclic N-Boc α-amino sulfoxide was prepared and this successful synthesis relied on the α-amino sulfoxide being part of a bicyclic [3.1.0] fused ring system that could not undergo α-elimination of the sulfoxide. the Partner Organisations 2014.

Copper Cyanide-Catalyzed Palladium Coupling of N-tert-Butoxycarbonyl-Protected α-Lithio Amines with Aryl Iodides or Vinyl Iodides

Treatment of (α-aminoalkyl)lithium reagents with aryl iodides in the presence of catalytic amounts of CuCN and PdCl2(PPh3)2 or [(p-MeOC6H4)3P]4Pd affords 2-aryl substituted amines in modest to good yields. The yields can be improved by use of softer ligands such as AsPh3 and SbPh3 or by use of bis(diphenylphosphino)ferrocene (dppf). Coupled products are obtained with electron-rich aryl iodides (XArI, X = Me, OMe), and the reaction fails with electron-poor aryl iodides (XArI, X = NO2, CO2Li). Treatment of the (α-aminoalkyl)lithium reagents with vinyl iodides and Pd(0)/dppf/ CuCN afforded the coupling products in low to modest yields.