57527-71-6

Usage

Uses

Used in Pharmaceutical Industry:
1'-HYDROXY-BICYCLOHEXYL-1-CARBONITRILE is used as an intermediate in the synthesis of 1'',2''-Dehydro Dicyclomine (D229530), which is an impurity of Dicyclomine (D439300, HCl). Dicyclomine is a compound utilized as a gastrointestinal antispasmodic antacid, helping to alleviate symptoms such as abdominal cramps, bloating, and discomfort associated with gastrointestinal spasms.
The application of 1'-HYDROXY-BICYCLOHEXYL-1-CARBONITRILE in the pharmaceutical industry is primarily due to its role in the synthesis of Dicyclomine, a compound with significant therapeutic benefits in treating gastrointestinal issues. By facilitating the production of Dicyclomine, 1'-HYDROXY-BICYCLOHEXYL-1-CARBONITRILE contributes to the development of effective treatments for various gastrointestinal disorders.

Upstream product

• 108-94-1 cyclohexanone 
• 50654-54-1 (cyanocyclohexyl)lithium 
• 766-05-2 cyclohexane carbonitrile 
• 5222-53-7 cyclohexane-1,1-dicarbonitrile 
• 676132-35-7 1-bromocyclohexane-1-carbonitrile 
• 111-24-0 1,5-dibromo-pentane 
• 1360557-39-6 1-(phenylsulfinyl)cyclohexanecarbonitrile 
• 1446698-42-5 1-(dimethylsilyl)cyclohexanecarbonitrile 

Downstream Products

• 66500-51-4 Bicyclohexyl-1'-ene-1-carbonitrile 
• 66500-78-5 Bicyclohexyl-1'-ene-1-carboxylic acid amide 

Relevant academic research and scientific papers

Sulfinylnitriles: Sulfinyl-metal exchange-alkylation strategies

Adding organolithiums, Grignard reagents, or zincates to sulfinylnitriles triggers a facile sulfinyl-metal exchange to afford N- or C-metalated nitriles. Sulfinyl-magnesium exchange-alkylations efficiently install quaternary and tertiary centers, even in

Nucleophilic addition of α-(dimethylsilyl)nitriles to aldehydes and ketones

α-Alkylated (dimethylsilyl)acetonitriles (Me2HSiCR 3R4CN) react spontaneously with aldehydes in DMSO to give β-hydroxynitriles in good to high yields. The addition to ketones is effectively promoted by using MgCl2/su

Nitrile alkylations through sulfinyl-metal exchange

Triple alkylation: Phenylsulfinyl- and phenylthioacetonitrile can function as trianion equivalents of acetonitrile by sequential alkylation and sulfinyl-metal exchange (see scheme; mCPBA=meta-chloroperoxybenzoic acid). The metalated nitriles alkylate a range of electrophiles to obtain nitriles with quaternary centers. The sulfinyl-metal exchange proceeds under very mild conditions and has a high functional-group tolerance. Copyright

Metalated nitriles: Organolithium, -magnesium? and -copper exchange of α-halonitriles

(Chemical Equation Presented) α-Halonitriles react with alkyllithium, organomagnesium, and lithium dimethylcuprate reagents generating reactive, metalated nitriles. The rapid halogen-metal exchange with alkyllithium and Grignard reagents allows selective exchange in the presence of reactive carbonyl electrophiles, including aldehydes, providing a high-yielding alkylation protocol. Lithiated and magnesiated nitriles react with propargyl bromide by SN2 displacement whereas organocopper nitriles react by S N2′ displacement, correlating with the formation of a C-metalated nitrile.

Metalated Nitriles: Halogen - Metal Exchange with α-Halonitriles

(Equation presented) α-Halonitriles react with organometallic reagents in a facile halogen-metal exchange. The halogen-metal exchange is extremely fast with Grignard and alkyllithium reagents, generating metalated nitriles in situ with aldehyde, ketone, a

A facile method for the construction of highly substituted acetonitriles and olefins. Malononitriles as acetonitrile carbanion and alkylidene dianion equivalents

The use of malononitrile to facilitate the preparation of highly substituted nitriles, via reductive alkylation/addition, and olefins, via a combination of reductive addition and reductive elimination, is described.