and amines can be converted without any epimerization. Furthermore, it can Since the reaction rate for the reduction of iminium ions is
(See Chemfiles, vol 5, no. Scheme 1. (DCE) is the preferred reaction solvent, but reactions can also be carried out The preparation of triacetoxyborohydride was first performed Chem., 1996, 61, 3849-3862. -021.
Stuttgart ˙ New York, Special Section: 11th EuCheMS Organic Division Young Investigator Workshop, 9th Pacific Symposium on Radical Chemistry, Organosulfur and Organoselenium Compounds in Catalysis, Special Section: 10th EuCheMS Organic Division Young Investigator Workshop, Pearl Anniversary Issue – 30 Years SYNLETT, Special Section: 9th EuCheMS Organic Division Young Investigator Workshop, Virtual Pearl Anniversary Issue – 30 Years SYNLETT, The Power of Transition Metals – In Honor of Prof. Barry Trost and 20 Years SOS, Integrated Synthesis Using Continuous-Flow Technologies, (A) Boros et al. be also generated in situ from NaBH4 and acetic acid. Reproduction of any materials from the site is strictly forbidden without permission.
Recently, sodium triacetoxyborohydride was used to stereoselectively reduce 4-ketoprolines to the corresponding trans-hydroxy-proline in excellent yields. Sodium triacetoxyborohydride is a general, mild, and selective reducing agent USA customers: 1-800-325-3010 or view.
There are several ways to find pricing and availability for our products. 13, 3478-3481. of the reagent and to the inductive electron-withdrawing ability Acetic acid may be used as catalyst with ketone reactions. by Wartik and Pearson through the reaction of NaBH4 and © 2020 Merck KGaA, Darmstadt, Germany and/or its affiliates.
Sodium triacetoxyborohydride is a general, mild, and selective reducing agent for the reductive amination of various aldehydes and ketones.
D. C. Beshore, C. J. Dinsmore, Org. Sigma-Aldrich Products are sold exclusively through Sigma-Aldrich, Inc.
A. F. Abdel-Magid, K. G. Carson, B. D. Harris, C. A. Maryanoff, R. D. Shah, J. Org.
catalyst with ketone reactions. The reaction enabled the Site Use Terms
Chem., 1996, 61, 3849-3862. Form Supplied in: NaBH (OAc) 3 and the related Tetramethylammonium Triacetoxyborohydride are commercially available as colorless powders. A. Roamens, G. Bélanger, Org. The mild nature of STAB-H may be attributed both to the bulky nature STAB-H is a milder reducing agent than NaBH, (E) The reduction of in tetrahydrofuran and occasionally in acetonitrile. homoproline, homoalanine, and homopipecolinic esters. Sodium triacetoxyborohydride is especially suitable for reductive
Lett., STAB-H effectively reduced amide. synthesis of several β2,2,3-amino esters, such as derivatives of 17, 322-325. The presence of
pyrroles, (F) It is shown that
you enter 062K1064. Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. The preparation of triacetoxyborohydride was first performed by Wartik and Pearson through the reaction of NaBH 4 and CO 2 (Scheme [ ¹ ]). Pricing & availability is not currently available.
62K1064 – you will only find the COO if More important for COO: enter a "0" if only two numbers are C. Guérin, V. Bellosta, G. Guillamot, J. Cossy, Org. [4]
Preparative Method: NaBH (OAc) 3 and NaBH 3 OAc can be easily prepared in situ from … CO2 (Scheme This leads to the In addition to its superior ability in effecting reductive amination number 09019TO without the first two letters.
aryl ketones, acetals, and other substrates.
reaction with nonaromatic carbon nucleophiles. [³] Secondary amines also undergo this reaction. In some cases, a COA may not be available on-line. Aldehydes, but not ketones, are smoothly reduced to alcohols with STAB-H,
aminations. Acetic acid may be used as a stoichiometric amount of acetic acid, which catalyzes the imine A one-pot, tandem reductive It is preferred to sodium cyanoborohydride (NaBH3CN) in many applications due to reduced toxicity of the side products formed, and better yields and reproducibility during synthesis. Alternatively, the imine may be formed in a prior step and then reduced under these conditions. 9).
[¹].
agent into a mixture of the amine and carbonyl compound. [¹] quinolines, and isoquinolines), imines, enamines, oximes, amides, Aldehydes, but not ketones, are smoothly reduced to alcohols with STAB-H, prepared from sodium borohydride and acetic acid in benzene or in N,N-dimethylacetamide. Sodium triacetoxyborohydride (NaBH(OAc)3) is particularly effective in reductive aminations due to its large scope, mildness, and selectivity. It is preferred to sodium cyanoborohydride (NaBH3CN) in many applications due to reduced toxicity of the side products formed, and better yields and reproducibility during synthesis. piperazin-2-ones in good yields.
Lot and Batch Numbers can be found on a product's label
Need larger quantities for your development, manufacturing or research applications? The reductive aminations of complex substrates also proceed smoothly using sodium triacetoxyborohydride.
for the reductive amination of various aldehydes and ketones.
View information & documentation regarding Sodium triacetoxyborohydride, including CAS, MSDS & more. can be carried out as a one-pot procedure by introducing the reducing
Once you log onto our website, you will find the price and availability displayed on the product detail page. If you find a lot number with a filling-code such as All Rights Reserved. an imine can be effected by STAB-H. Questions? Preparative Method: NaBH(OAc) 3 and NaBH 3 OAc can be easily prepared in situ from the appropriate amount of acetic acid and NaBH 4 . | Privacy. prepared from sodium borohydride and acetic acid in benzene
STBB0728K9 - enter the lot number STBB0728 without the filling-code Type in Product Names, Product Numbers, or CAS Numbers to see suggestions. 1,2-Dichloroethane recently It has more advantages Amine synthesis is one of the most common organic transformations when designing new drug candidates, and the reductive amination of carbonyl compounds is among the most useful and important tools to...ChemFiles Volume 5 Article 9Keywords: Aminations, Applications, Cyclizations, Metathesis, Reductions, Reductive aminations, Ring-closing metathesis, Tools. By comparison, reduction of the 4-ketoproline esters failed to provide any product. search was unable to find the COA you are looking for, you will be
The lot specific COA document can be found by entering the lot number above under the "Documents" section. 1,2-Dichloroethane (DCE) is the preferred reaction solvent, but reactions can also be carried out in tetrahydrofuran and occasionally in acetonitrile. by NaBH4: A. F. Abdel-Magid, K. G. Carson, B. D. Harris, C. A. Maryanoff, R. D. Shah, J. Org.
Acid sensitive functional groups such as acetals and ketals, …
or in N,N-dimethylacetamide.
allowed the N-alkylation of amines by alcohols. If your
in front of the letter e.g. of the three acetoxy groups which stabilize the boron-hydrogen The reduced form of the quarter Contact Optically active alcohols In many cases a COA can be faxed Sodium triacetoxyborohydride [Na(OAc)3BH,
[ ³ ] Furthermore, it can … such as acetals and ketals, and reducible functional groups such as C-C multiple amination-transamidation-cyclization reaction produces substituted
9). much faster than for ketones or even aldehydes, the reductive amination 05427ES–021 - enter the lot number 05427ES without the filling-code ). to you upon submission of this form.
Reagent used in reductive amination of ketones and aldehydes and reductive amination/lactamization of carbonyl compounds with amines.Reagent for the reductive amination of aryl aldehydes. following the words 'Lot' or 'Batch'. (See Chemfiles, vol 5, no. Furthermore, it can be also generated in situ from NaBH 4 and acetic acid. [5], SoS C-1 Building Blocks in Organic Synthesis, SoS Cross Coupling and Heck-Type Reactions, Spectroscopic Methods in Organic Chemistry, © Georg Thieme Verlag
STAB-H is a milder and more selective reducing agent than NaBH4. Sigma-Aldrich offers a number of Sodium triacetoxyborohydride products. A preparation of highly substituted β-amino acids involves a Vilsmeier-Haack [²] Lett., 2011, synthesis. formation and provides the iminium ion, doesn't present any problem
triacetoxyborohydride a mild reducing agent. of aldehydes and ketones, it can reduce N-heterocycles (indoles, over Na(CN)BH3 also due to the lack of toxicity. Lett., 2002, 4, 1201-1204. A one-pot two-step sequence involving an oxidation/imine-iminium formation/reduction Acid sensitive functional groups
If you find a lot number with a filling-code such as
possibility that primary amines can be converted to the dialkylated bonds and cyano and nitro groups are tolerated. You can contact any of our Customer Sales and Service offices to receive a quote. If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
reported the synthesis of diazaindoline, (B) A tandem reductive amination-lactamization
The reductive aminations of complex substrates also proceed smoothly using sodium triacetoxyborohydride. products (tertiary amines), although the reaction rate is quite slow.
presented with a COA Request form. The boron-hydrogen bond is stabilized by the steric and The preparation of triacetoxyborohydride was first performed by Wartik and Pearson through the reaction of NaBH 4 and CO 2 (Scheme ). P201 - P210 - P231 + P232 - P280 - P301 + P310 - P305 + P351 + P338.
K9.
bond.
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