147169-48-0

Upstream product

• 14649-03-7 1-phenylethylisocyanate 
• 75-65-0 tert-butyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 32366-25-9 1-azidoethylbenzene 
• 74651-77-7 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 1035813-57-0 C₁₁H₁₈NP 
• 216959-44-3 [tert-butoxycarbonyl-(1-phenyl-ethyl)-amino]-oxo-acetic acid ethyl ester 
• 618-36-0 rac-methylbenzylamine 
• 250296-58-3 N-tert-Butoxycarbonyl-N-trifluoromethylsulfonyl-4-trifluoromethylanilide 
• 40589-84-2 1-phenethyl urea 
• 1907-33-1 lithium tert-butoxide 
• 613-91-2 acetophenone oxime 
• 511244-42-1 N-(tert-butoxycarbonyl)-5,7-dinitroindoline 
• 98-85-1 1-Phenylethanol 

Downstream Products

• 182141-70-4 N-[(1S)-1-(4-bromophenyl)ethyl]-2,2,2-trifluoroacetamide 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 1292816-63-7 (S)-t-butyl N-(1-phenylethyl)-N-[(2-bromophenyl)methyl]carbamate 
• 618-36-0 rac-methylbenzylamine 

Relevant academic research and scientific papers

Highly Enantiospecific Borylation for Chiral α-Amino Tertiary Boronic Esters

Herein we report a highly efficient and enantiospecific borylation method to synthesize a wide range of enantiopure (>99 % ee) α-amino tertiary boronic esters. The configurationally stable α-N-Boc substituted tertiary organolithium species and pinacolborane (HBpin) underwent enantiospecific borylation at ?78 °C with the formation of a new stereogenic C?B bond. This reaction has a broad scope, enabling the synthesis of various α-amino tertiary boronic esters in excellent yields and, importantly, with universally excellent enantiospecificity (>99 % es) and complete retention of configuration.

Base-Mediated Intramolecular Decarboxylative Synthesis of Alkylamines from Alkanoyloxycarbamates

A general and effective method for the synthesis of alkylamine via intramolecular decarboxylation of alkanoyloxycarbamates is described. The alkanoyloxycarbamates are readily prepared with alkyl carboxylic acids and hydroxylamine. The reaction shows a broad range of substrates (primary and secondary alkyl) with functional tolerance, and the corresponding products were obtained in good yields under mild conditions.

Sustainable and chemoselective N-Boc protection of amines in biodegradable deep eutectic solvent

Abstract: A green and practical approach for the chemoselective N-tert-butyloxycarbonylation of structurally diverse amines with di-tert-butyl dicarbonate (Boc2O) is described. Selective N-Boc protection was achieved in excellent yields in urea-choline chloride deep eutectic solvent (DES) as the most promising environmentally benign and cost-effective solvent under mild reaction condition. DES can protect various aromatic and aliphatic amines using Boc2O in good to excellent yields in short reaction times without any side products. Graphical abstract: [Figure not available: see fulltext.].

Preparation, characterization and application of 1,4-disulfopiperazine-1,4-diium chloride ([Piper-(SO3H)2]·2Cl) as an efficient dicationic ionic catalyst for the N-Boc protection of amines

In this work, 1,4-disulfopiperazine-1,4-diium chloride ([Piper-(SO3H)2]·2Cl), as a novel Br?nsted acidic ionic catalyst is synthesized and characterized using a series of techniques including FT-IR, TGA, DTA, SEM, pH analysis and Hammett acidity function. This substance can significantly catalyze the N-Boc protection of amines without solvent interference at room temperature. The advantages of this manner are chemoselectivity, short reaction times, suitable yields, excellent yields of the products, without solvent interference and ease of preparation as well as reusability of the catalyst.

Synthesis of N-Boc-Propargylic and Allylic Amines by Reaction of Organomagnesium Reagents with N-Boc-Aminals and Their Oxidation to N-Boc-Ketimines

Previously inaccessible N-Boc-protected propargylic and allylic amines were synthesized by the reaction between N-Boc-aminals and organomagnesium reagents through the in situ generated N-Boc-imine intermediates. The obtained N-Boc-propargylic amines could be readily converted into unprecedented N-Boc-ketimines by oxidation with manganese dioxide.

Oxidative Amidation of Nitroalkanes with Amine Nucleophiles using Molecular Oxygen and Iodine

The formation of amides and peptides often necessitates powerful yet mild reagent systems. The reagents used, however, are often expensive and highly elaborate. New atom-economical and practical methods that achieve such goals are highly desirable. Ideally, the methods should start with substrates that are readily available in both chiral and non-chiral forms and utilize cheap reagents that are compatible with a wide variety of functional groups, steric encumberance, and epimerizable stereocenters. A direct oxidative method was developed to form amide and peptide bonds between amines and primary nitroalkanes simply by using I2 and K2CO3 under O2. Contrary to expectations, a 1:1 halogen-bonded complex forms between the iodonium source and the amine, which reacts with nitronates to form α-iodo nitroalkanes as precursors to the amides.

Rapid assessment of protecting-group stability by using a robustness screen

An experimentally simple method has been developed to rapidly establish the stability of widely utilized silyl, acetal, and carbamate protecting groups to a given set of reaction conditions. Assessment of up to twelve protecting groups in a single experiment has been demonstrated. Evaluation of this protocol in two unrelated synthetic transformations suggests that this method can be used to select appropriate protecting groups in the design of synthetic routes.

A simple, rapid, and efficient N-Boc protection of amines under ultrasound irradiation and catalyst-free conditions

A green and simple approach for the N-Boc protection on structurally diverse amines under ultrasound irradiation is described. Selective N-Boc protection was achieved in excellent isolated yield in a short reaction time at room temperature. Mild conditions, inexpensive and an easily available reagent, and absence of any auxiliary substances are the main advantages of this procedure. Graphical abstract: [Figure not available: see fulltext.]

Synthesis, X-ray crystallography, and reactions of N-acyl and N-carbamoyl succinimides

A collection of N-acyl and N-carbamoyl succinimides were prepared by acylation of succinimide with acyl chlorides or by ethylene dichloride (EDC) coupling of carboxylic acids. The x-ray crystal structures of N-benzoyl and N-p-nitrobenzoyl succinimides were determined. The N-acyl succinimides were effective in acylating primary amines, a secondary amine, and an aromatic amine. Copyright

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.