109774-57-4

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 100-46-9 benzylamine 
• 87100-28-5 pinacol benzylboronate 
• 51779-32-9 iminodicarboxylic acid di-tert-butyl ester 
• 100-39-0 benzyl bromide 
• 89004-82-0 potassium bis(tert-butoxycarbonyl)amide 
• 100-44-7 benzyl chloride 

Downstream Products

• 42116-44-9 N-tert-butoxycarbonylbenzylamine 
• 111652-10-9 tert-Butoxycarbonylamino-phenyl-acetic acid tert-butyl ester 
• 864871-38-5 diethyl 2-(1-(N-tert-butoxycarbonylamino)-1-phenylmethyl)malonate 
• 100-46-9 benzylamine 
• 102234-85-5 N-benzyl-N-methylammonium trifluoroacetate 
• 81616-14-0 tert-butyl N-benzyl-N-methylcarbamate 

Relevant academic research and scientific papers

Direct stereospecific amination of alkyl and aryl pinacol boronates

The direct amination of alkyl and aryl pinacol boronates is accomplished with lithiated methoxyamine. This reaction directly provides aliphatic and aromatic amines, stereospecifically, and without preactivation of the boronate substrate.

A facile synthesis of primary and secondary amines

A facile synthesis of primary amines (R-CH2-NH2, where R = napht-2-yl, anthr-9-yl, phenyl, p-nitrophenyl) and secondary amines (R-NH-R', where R is as mentioned above for primary amines and R' = methyl) is described. The primary amines were obtained by alkylation of di-tert-butyl imidodicarbonate (Boc2NH) under phase-transfer catalysis (PTC) conditions, followed by acidolytic removal of the amine protecting groups. The secondary amines were obtained from the appropriate primary amines by alkylation of their N-tert-butoxycarbonyl derivatives (Boc-NH-R), followed by Boc group acidolysis. It is worth emphasizing that the substrates for synthesis of secondary amines (Boc-NH-R) were obtained via selective removal of one of the tert-butoxycarbonyl groups from the alkylated di-tert-butyl imidodicarbonates (Boc2N-R).

A convenient synthesis of N-Boc-protected tert-butyl esters of phenylglycines from benzylamines

The N,N-di-Boc-protected benzylamines undergo [1,2] Boc migration on treatment with KDA/t-BuOLi. By this reaction, the corresponding N-Boc-protected t-butyl esters of phenylglycines are obtained in high yields.

A Convenient One-Flask Preparation of Di-t-butyl Iminodicarbonate: A Versatile Gabriel Reagent

An improved synthesis of di-t-butyl iminodicarbonate from formamide and di-t-butyl dicarbonate with dimethylaminopyridine as a catalyst followed by aminolytic removal of the formyl group is described as well as a few applications related to the synthesis of primary amines.

A Simple Method for tert-Butoxycarbonylation of Amides

The tert-butoxycarbonyl (Boc) function was conveniently introduced onto the amide nitrogen in several secondary amides using di-tert-butyl dicarbonate in dry acetonitrile with 4-dimethylaminopyridine as catalyst.Carboxamides with different acyl groups such as formyl, acetyl and benzoyl are presented as well as derivatives of carbamic acid.Examples also include other amide types: sulfonamide, sulfenamide and phosphinamide which were all smoothly converted to the corresponding Boc derivatives under these conditions.The yields were generally excellent and the resulting Boc analogues stable compounds which could be stored for months under ordinary conditions.Some stereochemical and structural aspects of this acylation are also discussed.Bulky substituents in the proximity of the amide moiety significantly retarded the reaction and in some cases no product was detected.For one compound with an activated methine group, C acylation was observed.