132629-17-5

Basic information

• Product Name: dimethyl 2-benzyl-2-(<11C>methyl)malonate
• Synonyms: dimethyl 2-benzyl-2-(<11C>methyl)malonate
• CAS NO: 132629-17-5
• Molecular Weight: 235.257
• Mol File: 132629-17-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: dimethyl 2-benzyl-2-(<11C>methyl)malonate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl 2-benzyl-2-(<11C>methyl)malonate(132629-17-5)
• EPA Substance Registry System: dimethyl 2-benzyl-2-(<11C>methyl)malonate(132629-17-5)

Safety Data

• Hazardous Substances Data: 132629-17-5(Hazardous Substances Data)

Upstream product

• 54245-42-0 [11C]methyl iodide 
• 49769-78-0 2-benzyl-malonic acid dimethyl ester 

Downstream Products

• 132629-19-7 monomethyl 2-benzyl-2-((¹¹C)methyl)malonic acid 
• 135154-83-5 2-benzyl-<3-11C>propionic acid 

Relevant articles and documents

Synthesis of Racemic (S)-(+)- or (R)-(-)-amphetamine

The synthesis of racemic (S)-(+)- or (R)-(-)-amphetamine (3) is reported.The alkylation of dimethyl 2-benzylmalonate with methyl iodide yielded dimethyl 2-benzyl-2-(methyl)malonate (1) which was used as an intermediate in the synthesis of 3.Hydrolysis of 1 with NaOH and subsequent decarboxylation using glacial acetic acid and heating produced 2-benzyl-propionic acid (2).Conversion of 2 into 3 was achieved via the intermediate isocyanate using diphenylphosphoryl azide (DPPA), and subsequently into the amine using conc.HCl.After purification by solid-phase extraction and preparative LC, (+/-)-3 was obtained with a radiochemical purity greater than 98percent.Starting with 3 GBq (81 mCi) carbon dioxide, 145 MBq (3.9 mCi) (+/-)-amphetamine was obtained in 45 min with a 22percent decay-corrected radiochemical yield.Enantiomerically pure 3 was obtained by the preparative LC separation of the (+)- or (-)-10-camphorsulfonamide derivatives of the racemate with a total decay-corrected radiochemical yield of 7percent (counted from the start of methyl iodide synthesis).In a typical synthesis, 27 MBq (0.7 mCi) enantiomerically pure (S)-(+)- or (R)-(-)-amphetamine were obtained starting from 3 GBq (81 mCi)carbon dioxide.The position of labelling was confirmed by a 13C synthesis using the same reaction pathway, and analysis by 13C NMR spectroscopy.