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Sodium triacetoxyborohydride is used as a reagent in reductive amination of ketones, aldehydes and lactamization of carbonyl compounds with amines. It also serves as a reducing agent in organic synthesis.
Selective reducing agent; review: Org. Prep. Proced. Int., 17, 317 (1985). Reduces aldehydes in the presence of ketones: J. Chem. Soc., Chem. Commun., 535 (1975). For stereoselective reduction of ketones in AcOH, see: Tetrahedron Lett., 273 (1983). Reduces ß-hydroxy ketones diastereoselectively to anti-diols: J. Am. Chem. Soc., 110, 3560 (1988), and cyclic ß-enamino esters selectively to the cis-amino esters: J. Org. Chem., 59, 5328 (1994); Tetrahedron: Asymmetry, 5, 1455 (1994).
Excellent reagent for reductive amination of aldehydes and ketones with a wide variety of amines: J. Org. Chem., 61, 3849 (1996); Tetrahedron Lett., 37, 3977 (1996); review: A.C.S. Symp. Ser., 641, 201 (1996).
Tahara, Y. K.; Ito, M.; Kanyiva, K. S.; Shibata, T. Total Synthesis of cis-Clavicipitic Acid from Asparagine via Ir-Catalyzed C-H bond Activation as a Key Step. Chem. Eur. J. 2015, 21 (32), 11340-11343.
Kang, B.; Oh, J. A.; Lee, J. Y.; Rhim, H.; Yune, T. Y.; Choo, H. Y. P. 3-Benzamides and 3, 4, 5-trimethoxyphenyl amines as calcium channel blockers. Bioorg. Med. Chem 2015, 23 (18), 6166-6172.
Hazard Statements: H228-H261-H315-H318-H335
Flammable solid. In contact with water releases flammable gas. Causes skin irritation. Causes serious eye damage. May cause respiratory irritation.
Precautionary Statements: P223-P210-P231+P232-P305+P351+P338-P405-P501a
Keep away from any possible contact with water, because of violent reaction and possible flash fire. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Handle under inert gas. Protect from moisture. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.