85231-92-1

Basic information

• Product Name: diethyl N-tert-butoxycarbonyl-N-phenylmethylphosphoramidate
• Synonyms: diethyl N-tert-butoxycarbonyl-N-phenylmethylphosphoramidate
• CAS NO: 85231-92-1
• Molecular Weight: 343.36
• Mol File: 85231-92-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: diethyl N-tert-butoxycarbonyl-N-phenylmethylphosphoramidate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl N-tert-butoxycarbonyl-N-phenylmethylphosphoramidate(85231-92-1)
• EPA Substance Registry System: diethyl N-tert-butoxycarbonyl-N-phenylmethylphosphoramidate(85231-92-1)

Safety Data

• Hazardous Substances Data: 85231-92-1(Hazardous Substances Data)

Upstream product

• 85232-03-7 Diethyl N-sodio-N-(tert-butoxycarbonyl)phosphoramidate 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 53640-96-3 diethyl N-benzylphosphoramidate 
• 42116-44-9 N-tert-butoxycarbonylbenzylamine 
• 814-49-3 diethyl chlorophosphate 
• 85232-02-6 diethyl N-tert-butyloxycarbonylphosphoramidate 
• 20039-33-2 diethoxyphosphoryl isocyanate 
• 100-46-9 benzylamine 
• 100-51-6 benzyl alcohol 

Downstream Products

• 14613-34-4 benzylamine p-toluenesulfonic acid 
• 134981-68-3 (+/-)-diethyl 1-(tert-butoxycarbonylamino)phenylmethylphosphonate 
• 18108-22-0 1-amino-1-phenylmethylphosphonic acid 
• 3287-99-8 benzylamine hydrochloride 
• 53640-96-3 diethyl N-benzylphosphoramidate 

Relevant articles and documents

New protocol for converting alcohols into amines

The reactions between diethyl N-(t-butoxycarbonyl)phosphoramidate 1, diisopropyl azodicarboxylate (DIAD), triphenylphosphine (TPP) and primary or secondary alcohols lead to the corresponding diethyl N-alkyl-N-(t-butoxycarbonyl)phosphoramidates 2a-o. Deprotection of crude 2 by refluxing with p-toluenesulfonic acid monohydrate in ethanol affords ammonium tosylates 3a-o in moderate to good overall yields. The N-alkylation of 1 proceeds stereoselectively with complete inversion of the configuration of the alkyl group.

Transformation of Arylmethylamines into α-Aminophosphonic Acids via Metalated Phosphoramidates: Rearrangement of Partly Configurationally Stable N-Phosphorylated α-Aminocarbanions

N-Benzyl phosphoramidate was protected at nitrogen with a TMS, p-toluenesulfonyl, Boc, lithium carboxylate, or diethoxyphosphinyl group and metalated with s-BuLi or LDA at -78 °C at the benzylic carbon. For the latter three protecting groups, the intermediate α-amino(phenylmethyl)-lithiums isomerized to N-protected α-aminophosphonates (phosphoramidate-aminophosphonate rearrangement). (R)-N-[1-2H1]Phenylmethyl phosphoramidate in combination with Boc or (EtO)2P-(O) was used to demonstrate that metalation occurs with a high primary kinetic isotope effect (kH/kD 13-50) and migration of the diethoxyphosphinyl group with retention of configuration at carbon. Furthermore, the short-lived carbanion lithium pairs are partly configurationally stable as the aminophosphonates formed with the two protecting groups have enantiomeric excesses of 79 and 24%, respectively. When homochiral lithium amides derived from (R)-N-isopropyl-1-phenylethylamine and (R,R)-N,N-di(1-phenylethyl)amine were used to induce a phosphoramidate-aminophosphonate rearrangement, chiral nonracemic α-aminophosphonates were formed (ee 26-35%). Three racemic aminophosphonates were deprotected with hot 6 M HCl and purified by ion-exchange chromatography on Dowex 50W,H+ to exemplify the transformation of phenyl-, p-tolyl-, and (1′-naphthyl)methylamine into aminophosphonic acids via lithiated phosphoramidates.

Diethyl N-(t-Butoxycarbonyl)-phosphoramidate: A New, Useful Substitute of Phthalimide in Gabriel-Type Syntheses of Primary Amines

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