3-Diethylaminopropyl alcohol

It is prepared by the interaction of 3,4,5-trimethoxybenzoyl chloride with 3-diethylaminopropyl alcohol with the elimination of hydrochloric acid. 

In a recent pubhcation the nitrile (EWG = CN) variant [ 126] of this chemistry was performed in water by applying N,N-diethylaminopropylated sihca gel as heterogeneous catalyst [ 128]. Another variant of this reaction sequence, leading to chiral sulfinylated enones, has been developed by Llera [ 129] employing the enantiomerically pure geminal bis(sulfoxide) 208 (Scheme 54). This bis(sulfoxide) was prepared from (-)-p-toluenesulfinic acid menthyl ester [100], as described by Kunieda [130]. Later this procedure was improved to increase the yield from 35 to 91% [13,131]. Treatment of 208 with enolizable aldehydes or ketones, in the presence of piperidine as a base and thiophile, initiated a reaction cascade involving a condensation step (to 210), a proton shift to allylic sulfoxide 211, and a [2,3]-0-shift followed by a piperidine-mediated desulfuration delivering the alcohols 212 as isomeric mixtures. Oxidation of the latter compounds (one of the R = H) led to enantiomerically pure E-y-oxo vinyl sulfoxides 213. 

Ammonium bicarbonate stock (100 mMl was made and stored at 4° C. Stock solutions of all proteins were prepared in 0.1% TFA, 50% acetonitrile solutions and stored at -20°C until use. Aliquots of the stocks, containing 10 to 100 pg of protein, were dried in a centrifugal dryer prior to digestion. To 5 mg of N,N-diethylaminopropyl-bis-(3-hydroxypropyl) phosphine, 1 ml of 50% isopropyl alcohol/50 mM ammonium bicarbonate was added. The samples were then resuspended in 20 pi reagent solution per 10 pg of protein, heated at 80 C for 2 hours, and dried to remove volatile components. 

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