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Biotage® MP-Cyanoborohydride

Powerful, Safe, and Efficient Cyanoborohydride Chemistry for Reductive Amination

MP-Cyanoborohydride

Biotage® MP-Cyanoborohydride is a macroporous polymer supported cyanoborohydride.  It is a versatile reducing agent for the reductive amination of carbonyl compounds and reduction of imines.  The reaction work-up protocol is greatly simplified by using the solid supported reagent. Specifically, compared with the small molecule sodium cyanoborohydride, it is reported that toxic cyanide is not released on reaction workup and therefore does not contaminate the product or pose a danger towards the user.

CONSUMABLES

Part No. Description Product type Pack Size Price
MP-Cyanoborohydride 800405 Biotage® MP-Cyanoborohydride, 10 g Consumables 1 Log in for price
MP-Cyanoborohydride 800406 Biotage® MP-Cyanoborohydride, 25 g Consumables 1 Log in for price
MP-Cyanoborohydride 800407 Biotage® MP-Cyanoborohydride, 100 g Consumables 1 Log in for price
MP-Cyanoborohydride 800408 Biotage® MP-Cyanoborohydride, 1 kg Consumables 1 Log in for price
MP-Cyanoborohydride 800511 Biotage® MP-Cyanoborohydride, 3 g Consumables 1 Log in for price

Committed to preserving our shared environment – further details available on request.

Can be used in processes in compliance with cGMP standards.

Manufacture of consumables is accredited by the world renowned British Standards Institute.

Flexible supply chains, back up manufacturing and warehousing ensures supply risk reduction

Can be used in processes in compliance with GLP standards.

Products which are scaleable from lab or development to process scale.

Long to indefinite product shelf life, reduced process risk.

Supports pharma guidelines for reducing elemental impurities in APIs.

Further extractable information provided on request.

Raw materials certified free of materials of human or animal origin.

Chemical substances used in our manufacturing process do not require registration.

Able to withstand mechanical stirring and heating under normal reaction conditions.

Download the product note.

 

Background

Biotage® MP-Cyanoborohydride is a macroporous polymer supported Cyanoborohydride, which is a solid-supported equivalent of tetraalkylammonium cyanoborohydride. The bound cyanoborohydride can be utilized as a versatile reducing agent for the reductive amination of carbonyl compounds and reduction of imines. Solid-supported cyanoborohydride can also be utilized for a number of other important reductive applications. Examples include reduction of a,b-unsaturated carbonyl compounds to the corresponding unsaturated alcohols, conversion of pyridinium ions to tetrahydropyridine derivatives, and dehalogenation reactions. The reaction work-up protocol is greatly simplified by using the solid supported reagent. Specifically, compared with the small molecule sodium cyanoborohydride, it is reported1 that toxic cyanide is not released on reaction workup and therefore does not contaminate the product or pose a danger towards the user.
The general protocol for the use of MP-Cyanoborohydride for reductive amination is summarized as below

Reactions are performed with 2.5 equivalents of MP-Cyanoborohydride relative to the limiting reagent. The carbonyl compound is used as the limiting reagent in the synthesis of secondary amines to suppress over alkylation. For tertiary amine synthesis, the carbonyl compound is used in excess to allow the use of catch-and-release purification with MP-TsOH cartridges4 or SCX cartridges. The reactions are carried out with at least 5 equivalents of HOAc to facilitate formation of imine or iminium ions, which undergo reduction with MP-Cyanoborohydride. Tetrahydrofuran (THF) is preferred to dichloroethane as solvent due to its greater stability in the presence of reactive amines. After reduction is complete, the crude reaction mixture is comprised of the product amine as an acetate salt and excess amine or carbonyl compound depending on the stoichiometry employed. At this point, there are several options for final purification.

Representative Procedures


Reductive Alkylation of Primary Amines 


To a 0.5 M THF solution of N-(3-aminopropyl)morpholine (1.2 mL, 0.60 mmol) was added 1.0 mL of a 0.5 M THF solution of cyclopentanone (0.50 mmol), 1.0 mL HOAc, and 1.0 mL THF. MP-Cyanoborohydride resin (0.5 g, 2.5 mmol/g, 1.25 mmol, 2.5 equivalents) was added and the reaction agitated at room temperature for 16 h. To the reaction mixture was added PS-Benzaldehyde (0.5 mmol) and the scavenging reaction mixture was stirred at room temperature for 16 h. The solution was filtered and the filtrate was concentrated to dryness. The crude product was dissolved in 2 mL of THF, and 0.89 g of MP-Carbonate (2.8 mmol/g, 2.5 mmol) was added. After 1.5 h the mixture was filtered and the filtrate was concentrated in vacuo to yield the desired secondary amine as a free base. The product secondary amine was characterized by gas chromatography and 1H NMR
For further information please see product note PPS392.