56553-60-7 Usage
Chemical Description
Sodium triacetoxyborohydride is a reducing agent used in organic synthesis.
Chemical Properties
Sodium triacetoxyborohydride (STAB-H) is commercially available as a hygroscopic white powder with a melting point of 116-120 °C. freely soluble in benzene. It is prepared by the reaction of NaBH4 with excess acetic acid in benzene or toluene.
Uses
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.
Application
Sodium triacetoxyborohydride is a mild reagent that exhibits remarkable selectivity as a reducing agent. It reduces aldehydes but not ketones; however, beta-hydroxyketones can be reduced selectively to give 1,3-trans diols.The steric and the electron-withdrawing effects of the three acetoxy groups stabilize the boron-hydrogen bond and are responsible for its mild reducing properties.Sodium triacetoxyborohydride or [NaBH(OAc)3] can be used as a reagent:In the reductive amination of ketones and aldehydes.To prepare N-benzyl-γ-valerolactam by reacting with methyl 4-oxopentanoate and benzylamine via reductive amination/lactamization.To reduce imines and enamines to corresponding amines.To reduce quinolines and isoquinolines to corresponding tetrahydro derivatives.In the hydroboration of alkenes.To synthesize nitroxide biradicals for creating high relaxivity terminal groups linkage to dendrimers.
Reactions
Sodium Triacetoxyborohydride is selective reducing agent in organic synthesis. It is especially suitable for reductive aminations. Since the reaction rate for the reduction of iminium ions is much faster than for ketones or even aldehydes, the reductive amination can be carried out as a one-pot procedure by introducing the reducing agent into a mixture of the amine and carbonyl compound. The presence of a stoichiometric amount of acetic acid, which catalyzes the imine formation and provides the iminium ion, doesn't present any problem under these conditions.Reductive amination (simplified)
Check Digit Verification of cas no
The CAS Registry Mumber 56553-60-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,6,5,5 and 3 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 56553-60:
(7*5)+(6*6)+(5*5)+(4*5)+(3*3)+(2*6)+(1*0)=137
137 % 10 = 7
So 56553-60-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H10BO6.Na/c1-11-4(8)7(5(9)12-2)6(10)13-3;/h7H,1-3H3;/q-1;+1/rC6H10BNaO6/c1-12-4(9)7(8,5(10)13-2)6(11)14-3/h7H,1-3H3
56553-60-7Relevant articles and documents
Gribble, G. W.,Ferguson, D. C.
, (1975)
Synthesis from (+)-α-pinene of optically active macrocycles containing cyclobutane, ester, azine, or hydrazide groups
Ishmuratov,Mingaleeva,Shakhanova,Muslukhov,Yakovleva,Botsman,Tolstikov
, p. 210 - 214 (2011)
Optically active symmetric macrocyclic diesterazines and diesterdihydrazides were synthesized efficiently from the available natural monoterpene (+)-α-pinene (de 50%) using a [2+1]-reaction of 1'-[(1S,3S)-3-(2-hydroxyethyl)-2,2-dimethylcyclobutyl]ethanone and glutaric and adipic acid chlorides followed by [1+1]-condensation of the intermediate diketodiesters with hydrazine hydrate or glutaric acid dihydrazide.
Two-step stereocontrolled synthesis of densely functionalized cyclic β-aminoesters containing four stereocenters, based on a new cerium(IV) ammonium nitrate catalyzed sequential three-component reaction
Sridharan, Vellaisamy,Menendez, J. Carlos
, p. 4303 - 4306 (2008)
(Chemical Equation Presented) The cerium(IV) ammonium nitrate (CAN)-catalyzed sequential, one-pot reaction between alkylamines, β-ketoesters, and chalcones afforded cis-4,6-disubstituted 2-alkylaminocyclohexene-1-carboxylic esters with complete diastereoselectivity. The carbon-carbon double bond of these compounds was reduced with sodium triacetoxyborohydride, again with complete diastereoselectivity. This novel two-step route allows the transformation of very simple acyclic starting materials into tetrasubstituted cyclohexane derivatives bearing four functional groups, including a cis-β-aminoester moiety, and generates four stereocenters, three of which are adjacent and one of which is quaternary.
Total Synthesis of Ritterazine B
Nakayama, Yasuaki,Maser, Michael R.,Okita, Tatsuya,Dubrovskiy, Anton V.,Campbell, Taryn L.,Reisman, Sarah E.
supporting information, p. 4187 - 4192 (2021/04/06)
The first total synthesis of the cytotoxic alkaloid ritterazine B is reported. The synthesis features a unified approach to both steroid subunits, employing a titanium-mediated propargylation reaction to achieve divergence from a common precursor. Other key steps include gold-catalyzed cycloisomerizations that install both spiroketals and late stage C-H oxidation to incorporate the C7′ alcohol.
Low-cost method preparation for doxazosin mesylate controlled release tablets
-
Paragraph 0017; 0018, (2019/07/01)
The invention relates to a preparation method of doxazosin mesylate controlled release tablets for treating urination disorder caused by prostatic hyperplasia, and belongs to the field of medicines. The invention provides a low-cost preparation method for doxazosin mesylate controlled release tablets.