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Sodium borohydride is an odorless white to gray-white microcrystalline powder that often forms lumps. It can be purified by recrystallization from warm (50 °C) diglyme . [ 10 ] Sodium borohydride is soluble in protic solvents such as water and lower alcohols.
α,β-Unsaturated nitro compounds can be reduced to saturated amines by: Catalytic hydrogenation over palladium-on-carbon; Iron metal; Lithium aluminium hydride [27] (Note: Hydroxylamines and oximes are typical impurities.) Lithium borohydride or sodium borohydride and trimethylsilyl chloride [28] Red-Al [29]
The imine is then reduced to an amine by sodium cyanoborohydride. This reaction works on both aldehydes and ketones. The carbonyl can be treated with ammonia, a primary amine, or a secondary amine to produce, respectively, 1°, 2°, and 3° amines. [5] Aromatic ketones and aldehydes can be reductively deoxygenated using sodium cyanoborohydride. [6]
Sodium borohydride can, under some circumstances, be used for ester reduction, especially with additives. [ 1 ] Forming aldehydes from carboxylic acid derivatives is challenging because weaker reducing agents (NaBH 4 ) are often very slow at reducing esters and carboxylic acids, whereas stronger reducing agents (LiAlH 4 ) immediately reduce the ...
The intermediate imine can be isolated or reacted in-situ with a suitable reducing agent (e.g., sodium borohydride) to produce the amine product. [2] Intramolecular reductive amination can also occur to afford a cyclic amine product if the amine and carbonyl are on the same molecule of starting material. [4]
The Narasaka–Prasad reduction, sometimes simply called Narasaka reduction, is a diastereoselective reduction of β-hydroxy ketones to the corresponding syn-dialcohols.The reaction employs a boron chelating agent, such as BBu 2 OMe, and a reducing agent, commonly sodium borohydride.
Microorganisms (or more specifically, their enzymes) reduce certain classes of simple ketones with extremely high enantioselectivity. Baker's yeast is the most common organism used to reduce ketones enzymatically, [18] [19] although other microorganisms may be used. Access to "unnatural" reduced enantiomers is difficult in most cases.
The compound is prepared by the reaction of tert-butylammonium chloride and sodium borohydride: [2] t-BuNH 3 Cl + NaBH 4 → t-BuNH 2 BH 3 + H 2 + NaCl. In organic synthesis, borane tert-butylamine can be used for selective reduction of certain functional groups including aldehydes, ketones, oximes, and imines. [3]