54256-51-8

Usage

Synthesis Reference(s)

Tetrahedron Letters, 27, p. 6369, 1986 DOI: 10.1016/S0040-4039(00)87811-9

InChI:InChI=1/C16H24O2/c1-3-4-5-6-7-8-9-14-10-12-15(13-11-14)16(17)18-2/h10-13H,3-9H2,1-2H3

Upstream product

• 30089-00-0 9-octyl-9-bora-bicyclo[3.3.1]nonane 
• 619-44-3 methyl 4-iodobenzoate 
• 98875-37-7 2-octyl-1,3,2-benzodioxaborole 
• 144493-15-2 4-oct-1-ynyl-benzoic acid methyl ester 
• 1192466-35-5 B-octyl-9-BBN-2-picoline complex 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 6018-41-3 methyl coumalate 
• 872-05-9 1-Decene 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 38841-98-4 n-octylmagnesium chloride 
• 66217-56-9 4,4,5,5-tetramethyl-2-octyl-[1,3,2]dioxaborolane 
• 111-66-0 oct-1-ene 
• 67-56-1 methanol 
• 3575-31-3 4-octylbenzoic acid 

Downstream Products

• 3575-31-3 4-octylbenzoic acid 
• 1313876-85-5 2,2-dimethyl-5-[2-(4-octylphenyl)ethyl]-1,3-dioxan-5-amine 
• 40016-26-0 1-chloromethyl-4-n-octylbenzene 
• 885605-36-7 5-(tert-butyloxycarbonylamino)-2,2-dimethyl-5-(4-octylphenethyl)-1,3-dioxane 
• 50606-97-8 p-n-octylbenzoyl chloride 
• 337980-66-2 3-(5-butylthiophen-2-yl)-5-(4-octylphenyl)-isoxazole 
• 137476-81-4 (R)-(-)-1,1'-binaphthyl-2,2'-diylbis<(p-octylbenzyl)diphenylphosphonium> dibromide 
• 137476-81-4 (S)-(+)-1,1'-binaphthyl-2,2'-diylbis<(p-octylbenzyl)diphenylphosphonium> dibromide 
• 137476-84-7 [2'-(Diphenyl-phosphinoyl)-[1,1']binaphthalenyl-2-yl]-(4-octyl-benzyl)-diphenyl-phosphonium; bromide 
• 88255-11-2 p-(n-octyl)benzyl bromide 

Relevant academic research and scientific papers

Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides

Suzuki cross-coupling of benzylic and unactivated aliphatic fluorides with aryl- and alkenylboronic acids has been achieved via mechanistically distinct Pd and Ni catalyzed pathways that outperform competing protodeboronation, β-hydride elimination, and h

Radical Chain Reduction via Carbon Dioxide Radical Anion (CO2?-)

We developed an effective method for reductive radical formation that utilizes the radical anion of carbon dioxide (CO2?-) as a powerful single electron reductant. Through a polarity matched hydrogen atom transfer (HAT) between an electrophilic radical and a formate salt, CO2?- formation occurs as a key element in a new radical chain reaction. Here, radical chain initiation can be performed through photochemical or thermal means, and we illustrate the ability of this approach to accomplish reductive activation of a range of substrate classes. Specifically, we employed this strategy in the intermolecular hydroarylation of unactivated alkenes with (hetero)aryl chlorides/bromides, radical deamination of arylammonium salts, aliphatic ketyl radical formation, and sulfonamide cleavage. We show that the reactivity of CO2?- with electron-poor olefins results in either single electron reduction or alkene hydrocarboxylation, where substrate reduction potentials can be utilized to predict reaction outcome.

Anti-Markovnikov hydroarylation of alkenes via polysulfide anion photocatalysis

A protocol for anti-Markovnikov hydroarylation of alkenes with aryl halides has been developed using polysulfide anions as photocatalysts in the presence of the Hantzsch ester and water under irradiation with visible light.

Synthesis of Fingolimod Employing Regioselective Aziridine Ring-Opening Reaction as a Key Step

An efficient and scalable synthesis of the immunomodulating drug fingolimod hydrochloride has been developed with the aziridine regioselective ring-opening reaction as a key step. This manuscript describes design, detailed synthetic route scouting, and optimization study of the aziridine ring-opening reaction. As a starting material for the polar part of the fingolimod molecule, cheap, common, and widely commercially available tris(hydroxymethyl)aminomethane was used. n-Octyl group was introduced into the molecule either via Kumada or Negishi cross-couplings, or alternatively by Sonogashira cross-coupling followed by hydrogenation. The final step consists of a one-pot acidic deprotection both of the acetonide and Boc group, providing thus highly pure fingolimod hydrochloride from the crude reaction mixture directly. The described process is highly effective, is industrially applicable, and has been successfully applied to 500 g scales of the target product.

Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Chlorides with Primary Alkyl Chlorides

Alkyl chlorides and aryl chlorides are among the most abundant and stable carbon electrophiles. Although their coupling with carbon nucleophiles is well developed, the cross-electrophile coupling of aryl chlorides with alkyl chlorides has remained a chall

Esterification of aryl/alkyl acids catalysed by n-bromosuccinimide under mild reaction conditions

N-halosuccinimides (NXSs) are well-known to be convenient, easily manipulable and low-priced halogenation reagents in organic synthesis. In the present work, N-bromosuccinimide (NBS) has been promoted as the most efficient and selective catalyst among the NXSs in the reaction of direct esterification of aryl and alkyl carboxylic acids. Comprehensive esterification of substituted benzoic acids, mono-, di- and tri-carboxy alkyl derivatives has been performed under neat reaction conditions. The method is metal-free, air- and moisture-tolerant, allowing for a simple synthetic and isolation procedure as well as the large-scale synthesis of aromatic and alkyl esters with yields up to 100%. Protocol for the recycling of the catalyst has been proposed.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Monofluoroalkyl Halides for Late-Stage Monofluoroalkylation

A combinatorial nickel-catalyzed monofluoroalkylation of aryl halides with unactivated fluoroalkyl halides by reductive cross-coupling has been developed. This method demonstrated high efficiency, mild conditions, and excellent functional-group tolerance, thus enabling the late-stage monofluoroalkylation of diverse drugs. The key to success was the combination of diverse readily available bidentate and monodentate pyridine-type nitrogen ligands with nickel, which in situ generated a variety of readily tunable catalysts to promote fluoroalkylation with broad scope with respect to both coupling partners. This combinatorial catalysis strategy offers a solution for nickel-catalyzed reductive cross-coupling reactions and provides an efficient way to synthesize fluoroalkylated druglike molecules for drug discovery.

Potentiation of the fosmidomycin analogue FR 900098 with substituted 2-oxazolines against Francisella novicida

A library of 33 compounds was screened for potentiation of the antibiotic FR 900098 against the Francisella tularensis surrogate Francisella novicida. From the screen a highly potent 2-oxazoline adjuvant was discovered capable of potentiating FR 900098 with a 1000-fold reduction in MIC against the Francisella sub-species F. novicida and F. philomiragia.

METHOD OF REGIOSELECTIVE SYNTHESIS OF SUBSTITUTED BENZOATES

A method of synthesis of para-substituted benzoate esters and acids is provided, wherein the para-substituted regioisomer is obtained substantially free of the meta-substituted impurity, the method comprising contacting a coumalate ester or acid and an un activated alkene at elevated temperature in the presence of a metal oxidation catalyst and an oxidant. The metal oxidation catalyst can be palladium, such as palladium on carbon, and the oxidant can be the oxygen gas in ambient air. The reaction can be carlied out without solvent or in high boiling hydrocarbon solvents such as mesitylene. When the un activated alkene is a monosubstituted alkene, yields of at least about 50 or 60% of para-substituted ester and acid products, respectively, are obtained, substantially free of the regioisomelic meta-substituted impurity.

A METHOD FOR THE PREPARATION OF FINGOLIMOD

The invention relates to a method of preparation of 2-amino-2-[2-(4-octylphenyl)- ethyl]propane-1,3-diol (I), comprising opening of the aziridine ring of the intermediates (LVI) by the treatment with organometallic compounds, preferably the Grignard reage