91230-12-5

Usage

Uses

Used in Pharmaceutical Synthesis:
Tert-butyl 1-phenylallylcarbamate is used as a protecting group for the amino group in the synthesis of a diverse range of pharmaceuticals and natural products. Its stable and easily removable nature makes it a popular choice for protecting the amino group in various organic reactions.
Used in Organic Chemistry:
Tert-butyl 1-phenylallylcarbamate is used as a valuable building block in organic chemistry for its versatility and utility in various synthetic pathways. It enables the development of new compounds and facilitates the synthesis of complex organic molecules.

Upstream product

• 4248-19-5 tert-butyl carbazate 
• 69562-10-3 1-phenyl-3-phenylseleno-1-propene 
• 1826-67-1 vinyl magnesium bromide 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 216959-34-1 ethyl 2-{[(tert-butoxy)carbonyl]amino}-2-oxoacetate 
• 51479-71-1 O-(3-Phenyl-2-propenyl)-2,2,2-Trichlorethanimidsaeure-O-(3-phenyl-2-propenyl)ester 
• 104-54-1 3-Phenylpropenol 
• 59874-90-7 N-<1-(1-phenylprop-2-enyl)> trichloroacetamide 
• 140196-38-9 1,1-dimethyl (2-oxo-1-phenylethyl)carbamate 
• 19493-09-5 Methylenetriphenylphosphorane 
• 73210-14-7 N-chloro-N-sodio-tert-butylcarbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4393-21-9 1-(phenyl)allylamine 

Downstream Products

• 374725-03-8 tert-butyl (-formyl-1-phenylethyl)carbamate 
• 172613-65-9 N-(2-oxo-1-phenyl-1-propyl)-carbamic acid tert-butyl ester 
• 136755-33-4 erythro-5-(α-t-butoxycarbonylamino)benzyl-3-chloro-2-isoxazoline 
• 136755-33-4 threo-5-(α-t-butoxycarbonylamino)benzyl-3-chloro-2-isoxazoline 
• 1620488-67-6 C₁₅H₂₁N₅O₄ 
• 1620488-58-5 tert-butyl (3-azido-1-phenylpropyl)carbamate 
• 218449-48-0 (3-hydroxy-1-phenylpropyl)carbamate tert-butyl ester 
• 1620488-61-0 3-azido-1-phenylpropylamine 
• 1630028-91-9 C₆H₁₁NO₅*C₉H₁₂N₄ 
• 1620488-63-2 N-(3-azido-1-phenylpropyl)-2-hydroxyiminoacetamide 
• 1609974-84-6 C₃₄H₅₆ClF₂NO₃S₂ 
• 1357590-19-2 C₂₂H₃₃NO₆S₃ 
• 1042039-30-4 dithiocarbonic acid S-[1-(tert-butoxycarbonylamino-phenyl-methyl)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl] ester O-ethyl ester 
• 136755-37-8 threo-3-methoxy-5-(α-trichloroacetamido)benzyl-2-isoxazoline 

Relevant academic research and scientific papers

N-Methyl Allylic Amines from Allylic Alcohols by Mitsunobu Substitution Using N-Boc Ethyl Oxamate

We report the practical, scalable synthesis of a range of N-methyl allylic amines. Primary and secondary allylic alcohols underwent a regioselective Mitsunobu reaction with readily accessible N-Boc ethyl oxamate to deliver the corresponding N-Boc allylic amines, including in enantiopure form via stereospecific substitution. Subsequent N-methylation and Boc deprotection without chromatography yielded the amine products as hydrochloride salts. This method solves the problem of converting commercially available alcohols into often volatile N-methyl allylic amines, many of which have limited commercial availability.

Enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides

In order to synthesize N-(3-azido-1-phenylpropyl)-2-hydroxyiminoacetamide, a key compound for the preparation of acetylcholinesterase (AChE) reactivators of the N-substituted 2-hydroxyiminoacetamide type, it was necessary to develop a method for forming a

Palladium-catalyzed anti-markovnikov oxidation of allylic amides to protected β-amino aldehydes

A general method for the preparation of N-protected β-amino aldehydes from allylic amines or linear allylic alcohols is described. Here the Pd(II)-catalyzed oxidation of N-protected allylic amines with benzoquinone is achieved in tBuOH under ambient conditions with excellent selectivity toward the anti-Markovnikov aldehyde products and full retention of configuration at the allylic carbon. The method shows a wide substrate scope and is tolerant of a range of protecting groups. Furthermore, β-amino aldehydes can be obtained directly from protected allylic alcohols via palladium-catalyzed autotandem reactions, and the application of this method to the synthesis of β-peptide aldehydes is described. From a mechanistic perspective, we demonstrate that tBuOH acts as a nucleophile in the reaction and that the initially formed tert-butyl ether undergoes spontaneous loss of isobutene to yield the aldehyde product. Furthermore, tBuOH can be used stoichiometrically, thereby broadening the solvent scope of the reaction. Primary and secondary alcohols do not undergo elimination, allowing the isolation of acetals, which subsequently can be hydrolyzed to their corresponding aldehyde products.

Aldehyde selective Wacker oxidations of phthalimide protected allylic amines: A new catalytic route to β3-amino acids

(Chemical Equation Presented) A new method for the synthesis of β3-amino acids is presented. Phthalimide protected allylic amines are oxidized under Wacker conditions selectively to aldehydes using PdCl2 and CuCl or Pd(MeCN)2/s

Synthesis of DL-Statine and DL-4-Amino-3-hydroxy-4-phenylbutanoic Acids via the Isoxazoline Route

1,3-Dipolar cycloaddition of chloronitrile oxide to N-allyltrichloroacetamides and subsequent reductive cleavage of the 3-methoxy-substituted isoxazolines gives methyl 3-hydroxy-4-trichloroacetamido esters which by acidic hydrolysis give the corresponding

Allylic Selenides in Organic Synthesis: New Methods for the Synthesis of Allylic Amines

Oxidative rearrangement of allylic selenides in the presence of various amine nucleophiles provides synthetic access to a variety of allylic amine derivatives.The stereochemical outcome of these reactions has been investigated, and is consistent with a -sigmatropic rearrangement mechanism.Several D-α-amino acids and racemic β,γ-unsaturated α-amino acids were prepared in this manner.A variant of this process employing an achiral allylic selenide and chiral amide afforded protected allylic amines in low diastereoisomeric excess.

Preparation of Protected Allylic Primary Amines from Allylic Phenyl Selenides

The reaction of an allylic selenide with an excess of an O-alkyl-N-chloro-N-sodiocarbamate in methanol affords an alkoxycarbonyl-protected allylic primary amine with allylic transposition.The preparation of several tert-butoxycarbonyl- and benzyloxycarbon