415679-46-8

Upstream product

• 105-14-6 5-diethylamino-2-pentanone 
• 626-95-9 1,4-Pentanediol 
• 109-89-7 diethylamine 
• 15146-94-8 5-chloro-2-pentanol 
• 5891-21-4 5-chloro-2-pentanone 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 23999-02-2 3-Ethoxycarbonyl-N,N-diethyl-4-oxopentylamine 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 112146-12-0 4-hydroxy-valeric acid diethylamide 
• 96-47-9 2-methyltetrahydrofuran 

Downstream Products

• 2920-50-5 Diethyl-{4-[phenyl-(2-trifluoromethyl-phenyl)-methoxy]-pentyl}-amine 
• 3216-08-8 Diethyl-{4-[phenyl-(3-trifluoromethyl-phenyl)-methoxy]-pentyl}-amine 

Relevant academic research and scientific papers

The effects of a hydroxyl group on some chemical and biological properties of n-pentyl ammonium salts

The effects of a hydroxyl group on the activity and affinity of compounds related to n-pentyltrimethylammonium have been studied on the guinea pig ileum, frog rectus, acetylcholinesterase and on partitioning (Rm) and size (Φ(v0), Vm). The hydroxyl group lowered affinity in all tests, confirming the importance of hydrophobic forces in binding to receptors. Activity on the ileum was lowered appreciably but on the rectus only slightly. The effects on Rm did not indicate any interactions between hydroxyl, onium group and water but the apparent size of the hydroxyl group (ΔΦ(v0)) depends on the nature of the onium group.

Reductive hydroxyalkylation/alkylation of amines with lactones/esters

We have developed a one-pot method for the direct intermolecular reductive hydroxyalkylation or alkylation of amines using lactones or esters as the hydroxyalkylating/alkylating reagents. The method is based on the in situ amidation of lactones/esters with DIBAL-H-amine complex (for primary amines) or DIBAL-H-amine hydrochloride salt complex (for secondary amines), followed by reduction of the amides with an excess of DIBAL-H. Different from the reduction of Weinreb amides with DIBAL-H where aldehydes are formed, the reduction of the in situ formed Weinreb amides yielded amines. Moreover, this method is not limited to Weinreb amides, instead, it also works for other amides in general. A plausible mechanism is suggested to account for the outcome of the reactions.

Detritylation Procedure under Non-Acidic Conditions: Naphthalene Catalysed Reductive Cleavage of Trityl Ethers

The reaction of primary, secondary, allylic and benzylic trityl ethers 1 with lithium powder and a catalytic amount of naphthalene led to reductive cleavage of the trityl-oxygen bond, affording the corresponding alcohols 2 in good to excellent yields under very mild reaction conditions. The detritylation process could successfully be extended to several hydroxy, alkoxy and amino functionalised trityl ethers. This methodology represents a new and efficient detritylation procedure under non-acidic reaction conditions.