58692-63-0

Upstream product

• 58692-61-8 (2-Bromo-1-phenyl-ethyl)-phosphoramidic acid diethyl ester 
• 478538-80-6 1-bromo-2-(tert-butoxycarbonyl)amino-2-phenyl ethane 

Relevant academic research and scientific papers

Ionic addition of t-butyl N,N-dibromocarbamate (BBC) to alkenes and cycloalkenes

The addition of t-butyl N,N-dibromocarbamate (BBC) to alkenes and cycloalkenes in the presence of BF3·Et2O proceeds smoothly at -20°C in CH2Cl2 affording upon reduction with aqueous Na2SO3 the corresponding β-bromo-N-Boc- amines. Immediate deprotection of these adducts with gaseous HCl yields β-bromoamine hydrochlorides in moderate yields. The regioselectivity typical for Markovnikov addition was observed for styrene. Stereospecific anti-addition of BBC to cyclohexene and (E)-hex-3-ene, as proven by 1H NMR evidence, is compatible with an ionic addition pathway and can be rationalized by assuming the intermediate complex formation between BBC and BF3.

Potential GABAB receptor antagonists. IX: The synthesis of 3-amino-3-(4-chlorophenyl)propanoic acid, 2-amino-2-(4-chlorophenyl)ethylphosphonic acid and 2-amino-2-(4-chlorophenyl)ethanesulfonic acid

This paper describes the synthesis of 3-amino-3-(4-chlorophenyl)propanoic acid and the corresponding phosphonic and sulfonic acids, lower homologues of baclofen, phaclofen and saclofen respectively. The chlorinated acids were all weak specific antagonists of GABA at the GABAB receptor, with the sulfonic acid (pA2 4·0) being stronger than the phosphonic acid (pA2 3·8) and carboxylic acid (pA2 3·5).

N,N-DIHALOPHOSPHORAMIDES - XVI IONIC ADDITION OF DIETHYL N,N-DIBROMOPHOSPHOROAMIDATE (DBPA) TO ALKENES AND CYCLOALKENES

The addition of DBPA to a variety of phenylethylenes, straight-chain terminal and nonterminal alkenes as well as cycloalkenes in the presence of boron trifluoride etherate has been investigated.It was found that the reaction proceeds smoothly at -20 deg C by adding an olefin to the solution of equimolar amounts of DBPA and boron trifluoride etherate in tetrachloromethane.N-Bromoadducts (mixtures or single isomers depending upon the structure of the olefin) initially formed could be reduced in situ with sodium bisulphite solution to give the corresponding diethyl N-(β-bromoalkyl)phosphoroamidates which in turn afforded β-bromoamine hydrochlorides upon treatment with hydrogen chloride in benzene at room temperature.The regiospecificity typical for Markovnikov addition, as proven by NMR and MS evidence, was observed for unsymmetrical phenylethylenes.The addition of DBPA to (E)-1-phenylpropene, (E)-2-butene, and (Z)-2-butene was also found to proceed stereospecifically affording the corresponding anti-adducts.These results are fully compatible with an ionic addition pathway and can be rationalized by assuming the intermediate formation of an electrophilic complex between DBPA and boron trifluoride.The reaction offers a new approach to aminobromination of alkenes and cycloalkenes and makes possible an easy access to β-bromoamines, the convenient precursors of aziridines.