Succinimide for NHS Esterification and Trifluoroacetylation
TFA-NHS [S0915] is utilized not only in the esterification of carboxy groups to form NHS esters, but also in the trifluoroacetylation of amines. Furthermore, it has been reported that TFA-NHS can both protect the amino group and activate the carboxy group of aminocarboxylic acids simultaneously. In the presence of pyridine, the reaction of an excess amount of TFA-NHS with an aminocarboxylic acid provides the resulting N-TFA-protected aminocarboxylic acid NHS ester in a one-pot process.
TCI Practical Example: Condensation Using DCC and HOBt
We are proud to present the amidation reaction using DCC [D0436] as a condensing agent, and HOBt [H0468] as an activator. The reaction report is actually performed by TCI's synthesis staff. In addition to the experimental procedure you can also see comments and analysis data from our staff.
The Luche reduction is a regioselective reduction of α,β-unsaturated ketones to afford allyl alcohols. When α,β-unsaturated ketones are reduced using sodium borohydride [S0480], 1,4-reduction is preferred over 1,2-reduction. It is considered that since the hydride of sodium borohydride is a “soft” nucleophile, the reaction proceeds at the β-position of the carbonyl compounds, which prefers a “soft” nucleophile. However, the hydride turns to “hard” in the presence of cerium(III) chloride [C2058] and an alcohol solvent, resulting in preferential 1,2-reduction.