Sodium triacetoxyborohydride

Description

Sodium triacetoxyborohydride (STAB) is a mild reducing agent that is commonly used in reductive aminations. STAB has the advantage over sodium cyanoborohydride (NaBH3CN) of not producing toxic side-pdts. One disadvantage of STAB is that it is H2O sensitive, not compatible with MeOH, and reacts slowly with EtOH and isopropanol. For these reasons STAB is typically used with aprotic solvents such as DCE, DCM, THF, dioxane, or toluene.

The Uses of Sodium triacetoxyborohydride

Sodium Triacetoxyborohydride(STAB) is a hydride reagent used in stereoselective reductive amination. It is able to replace toxic sodium cyanoborohydride under most conditions. It is selective in reducing aldehydes to alcohols in the presence of ketones. STAB is also stable in anhydrous acids, which enables reductive amination of aldehydes and ketones. It used in reductive amination of ketones and aldehydes and reductive amination/lactamization of carbonyl compounds with amines. The advantage of STAB compared to sodium cyanoborohydride is evident. STAB, being non-toxic, is easier to handle and forms no toxic by-products, making the treatment of process waste after the reaction simple and less costly.

The Uses of Sodium triacetoxyborohydride

A slurry of the amine (50 mg, 0.12 mmol) and the aldehyde (31.6 mg, 0.18 mmol) in 1,4-Dioxane (3 mL) was stirred for 5 min then treated with NaBH(OAc)3 (77 mg, 0.363 mmol). After stirring 10 min, DCM was added to the reaction mixture. The resulting solution was washed with saturated aq NaHCO3, water, and brine. The organics were dried (MgSO4) and concentrated in vacuo to provide the product which was used in the next step without further purification.

What are the applications of Application

Sodium triacetoxyborohydride is a reagent used for reductive amination of carbonyl compounds with amines