4151-44-4

Upstream product

• 50-00-0 formaldehyd 
• 102-97-6 Benzyl-isopropyl-amin 
• 103-67-3 benzyl-methyl-amine 
• 75-26-3 isopropyl bromide 
• 75-16-1 methylmagnesium bromide 
• 100-39-0 benzyl bromide 
• 75-07-0 acetaldehyde 
• 333-27-7 methyl trifluoromethanesulfonate 
• 108-10-1 4-methyl-2-pentanone 
• 67-64-1 acetone 
• 4747-21-1 N-methylpropan-2-amine 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.

Reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3as a reductant

Herein, we report the first example of efficient reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3 as a catalyst and a reductant under mild conditions, affording various tertiary and secondary amines in excellent yields. A mechanistic study indicates that BH3N(C2H5)3 plays a dual function role of promoting imine and iminium formation and serving as a reductant in reductive amination. This journal is

Expanding Water/Base Tolerant Frustrated Lewis Pair Chemistry to Alkylamines Enables Broad Scope Reductive Aminations

Lower Lewis acidity boranes demonstrate greater tolerance to combinations of water/strong Br?nsted bases than B(C6F5)3, this enables Si?H bond activation by a frustrated Lewis pair (FLP) mechanism to proceed in the presence of H2O/alkylamines. Specifically, BPh3has improved water tolerance in the presence of alkylamines as the Br?nsted acidic adduct H2O–BPh3does not undergo irreversible deprotonation with aliphatic amines in contrast to H2O–B(C6F5)3. Therefore BPh3is a catalyst for the reductive amination of aldehydes and ketones with alkylamines using silanes as reductants. A range of amines inaccessible using B(C6F5)3as catalyst, were accessible by reductive amination catalysed by BPh3via an operationally simple methodology requiring no purification of BPh3or reagents/solvent. BPh3has a complementary reductive amination scope to B(C6F5)3with the former not an effective catalyst for the reductive amination of arylamines, while the latter is not an effective catalyst for the reductive amination of alkylamines. This disparity is due to the different pKavalues of the water–borane adducts and the greater susceptibility of BPh3species towards protodeboronation. An understanding of the deactivation processes occurring using B(C6F5)3and BPh3as reductive amination catalysts led to the identification of a third triarylborane, B(3,5-Cl2C6H3)3, that has a broader substrate scope being able to catalyse the reductive amination of both aryl and alkyl amines with carbonyls.

Application of Grignard reagents to the synthesis of tertiary methylamines via resin-bound oxyiminium ions

The solid-phase synthesis of tertiary methylamines via the nucleophilic displacement of benzotriazole Mannich adducts with Grignard reagents using a hydroxylamine linker is described. The chemistry is exemplified by the synthesis of the MAO inhibitor α-methylpargyline. Also described is the synthesis of the analgesic Tramadol by an alternative one-pot solid-phase Mannich reaction. (C) 2000 Elsevier Science Ltd.

Intramolecular motions in a series of crystalline benzylammonium bromides and dibenzylamines studied by CP/MAS NMR

A series of 15 compounds including ammonium bromides containing one or two benzyl groups with H, methyl, isopropyl, tert-butyl and tert-amyl substituents and dibenzylamihe with N-isopropyl-, N-tert-butyl- and N-tert-amyl substituents have been synthesised and studied by CP/MAS NMR. The results of dynamic NMR studies on the solids suggest that there is a dramatically wide range of molecular motions occurring in this simple series of compounds: A combination of 2D CPEXSY, dynamic line shape analyses and T1ρ measurements reveals the considerable extent of intramolecular group motions including rotations of methyl, tert-butyl, tert-amyl and phenyl groups. Rates of rotation and activation parameters for these molecular motions are derived where appropriate. In the case of benzyl-tert-butylammonium bromide, where two independent molecules of the compound exist in the asymmetric unit it is shown that the independent processes of tert-butyl rotation in the two molecules have vastly different activation energies that differ by ca. 16 kJ mol-1. The extent of the motions observed suggests that commonly held prejudices about the rigidity of molecules in crystalline solids need revising.

On the Racemization of α-Hetero-Substituted Benzyllithium Compounds

Benzyllithium compounds carrying a benzylthio substituent (6), a benzylseleno substituent (8), and an isopropyl(methyl)amino substituent 14 have been generated.Racemization barriers have been determined in THF by monitoring the coalescence of signals of d

Lacrimal secretion stimulant (lss)

Ophthalmic compositions useful as tear stimulants when topically applied to the eye for effective treatment of dry eye syndrome.

Latent inhibitors of aldehyde dehydrogenase as alcohol deterrent agents

A series of compounds structurally related to pargyline (N-methyl-N-propargylbenzylamide) were synthesized with the propargyl group replaced by a cyclopropyl, allyl, or 2,2,2-trichloroethyl group and, additionally in several cases, with the methyl group r