220858-76-4

Basic information

• Product Name: 1-(tert-butyloxycarbonyl)-α-(R)-phenyl-2-(R)-piperidineacetic acid
• Synonyms: 1-(tert-butyloxycarbonyl)-α-(R)-phenyl-2-(R)-piperidineacetic acid
• CAS NO: 220858-76-4
• Molecular Weight: 319.401
• Mol File: 220858-76-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-(tert-butyloxycarbonyl)-α-(R)-phenyl-2-(R)-piperidineacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(tert-butyloxycarbonyl)-α-(R)-phenyl-2-(R)-piperidineacetic acid(220858-76-4)
• EPA Substance Registry System: 1-(tert-butyloxycarbonyl)-α-(R)-phenyl-2-(R)-piperidineacetic acid(220858-76-4)

Safety Data

• Hazardous Substances Data: 220858-76-4(Hazardous Substances Data)

Upstream product

• 757230-45-8 salt of (R,R)-N-Boc-ritalinic acid and (S)-1-phenylamine 
• 220858-72-0 3-<7-chloro-3-(S)-(methylsulfonyl)oxy-2-(R)-phenylheptanoyl>-4-(R)-phenyl-2-oxazolidinone 
• 220858-71-9 3-<7-chloro-3-(S)-hydroxy-2-(R)-phenylheptanoyl>-4-(R)-phenyl-2-oxazolidinone 
• 220858-74-2 β-(R)-phenyl-1-(phenylmethyl)-2-(R)-piperidineethanol 
• 220858-73-1 α-(S)-(4-chlorobutyl)-β-(S)-(hydroxymethyl)benzeneethanol methanesulfonate 
• 220858-75-3 β-(R)-phenyl-2-(R)-piperidineethanol 
• 161745-73-9 (4R)-3-phenylacetyl-4-phenyl-1,3-oxazolidin-2-one 
• 103-82-2 phenylacetic acid 
• 950206-44-7 C₂₈H₃₄O₂Si 
• 950206-43-6 C₁₂H₁₆O₂ 
• 950206-50-5 C₃₄H₄₅NO₃Si 
• 950206-49-2 C₂₉H₃₇NOSi 
• 950206-48-1 C₂₉H₃₅NO₂Si 
• 950206-47-0 C₂₉H₃₃NO₂Si 

Downstream Products

• 19262-68-1 dexmethylphenidate hydrochloride 
• 237419-31-7 (R)-2-((R)-Methoxycarbonyl-phenyl-methyl)-piperidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Concise and facile synthesis of (R,R)-dexmethylphenidate hydrochloride and its three stereoisomers

A new and concise route is reported for the first time for the preparation of four stereoisomers of dexmethylphenidate hydrochloride starting from a single reactant, 2-benzyolpyridine, through an eight-step reaction process, which includes hydrogenation,

Process for the preparation of dexmethylphenidate hydrochloride

The present invention provides a new and efficient process for the preparation of the dexmethylphenidate hydrochloride with high optical purity, the process comprising: (a) reacting a solution of threo-N-Boc-ritalinic acid with (S)-1-phenylethylamine, separating precipitated solid salt of (R,R)-enriched N-Boc-ritalinic acid with (S)-1-phenylethylamnine from the reaction mixture and recrystallizing, reslurring and/or trituring of said salt; (b) mixing the solid salt of (R,R)-N-Boc-ritalinic acid and (S)-1-phenylethylamine obtained in step (a) with aqueous acid and separating (R,R)-N-Boc-ritalinic acid from the mixture; and (c) reacting the (R,R)-N-Boc-ritalinic acid prepared in step (b) with hydrogen chloride and methanol to give dexmethylphenidate hydrochloride with optical purity of at least 99% ee. The present invention further provides salt of (R,R)-N-Boc-ritalinic acid with (S)-1-phenylethylamine as new intermediate in the preparation of dexmethylphenidate hydrochloride.

Asymmetric synthesis and pharmacology of methylphenidate and its para- substituted derivatives

We report the first asymmetric synthesis of the individual enantiomers of methylphenidate (1). From d-pipecolic acid, the (2R,2'R) and (2S,2'R) enantiomers of 1 were obtained in >99% optical purity while the (2S,2'S) and (2R,2'S) enantiomers of 1 were der