130459-53-9

Basic information

• Product Name: (1R,2S)-2-(tert-butoxycarbonyl(methyl)amino)-1-phenyl-1-propanol
• Synonyms: (1R,2S)-2-(tert-butoxycarbonyl(methyl)amino)-1-phenyl-1-propanol
• CAS NO: 130459-53-9
• Molecular Weight: 265.353
• Mol File: 130459-53-9.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (1R,2S)-2-(tert-butoxycarbonyl(methyl)amino)-1-phenyl-1-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-2-(tert-butoxycarbonyl(methyl)amino)-1-phenyl-1-propanol(130459-53-9)
• EPA Substance Registry System: (1R,2S)-2-(tert-butoxycarbonyl(methyl)amino)-1-phenyl-1-propanol(130459-53-9)

Safety Data

• Hazardous Substances Data: 130459-53-9(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 299-42-3 ephedrine 
• 321-97-1 (1R,2R)-pseudoephedrine 

Downstream Products

• 1201-56-5 (1S,2S)-N-Methylpseudoephedrine 
• 16251-47-1 (4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one 
• 91049-48-8 (4R,5S)-3,4-dimethyl-5-phenyloxazolidin-2-one 
• 91049-51-3 (4R,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one 

Relevant articles and documents

A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions

A general formamide-catalyzed protocol for the efficient transformation of alcohols into alkyl chlorides, which is promoted by substoichiometric amounts (down to 34 mol %) of inexpensive trichlorotriazine (TCT), is introduced. This is the first example of a TCT-mediated dihydroxychlorination of an OH-containing substrate (e.g., alcohols and carboxylic acids) in which all three chlorine atoms of TCT are transferred to the starting material. The consequently enhanced atom economy facilitates a significantly improved waste balance (E-factors down to 4), cost efficiency, and scalability (>50 g). Furthermore, the current procedure is distinguished by high levels of functional-group compatibility and stereoselectivity, as only weakly acidic cyanuric acid is released as exclusive byproduct. Finally, a one-pot protocol for the preparation of amines, azides, ethers, and sulfides enabled the synthesis of the drug rivastigmine with twofold SN2 inversion, which demonstrates the high practical value of the presented method.

Thioglycoluril as a highly efficient, recyclable and novel organocatalyst for N-Boc protection of amines

A simple and efficient protocol for the chemoselective mono-N-Boc protection of various structurally diverse amines with di-tert-butyl dicarbonate using thioglycoluril as the catalyst is described. The catalyst can be readily separated from the reaction products by simple filtration and recovered for reuse. No competitive side reactions, such as formation of isocyanate, urea, oxazolidinone, and N,N-di-Boc derivatives were observed.

Experimental and DEE study of the conversion of ephedrine derivatives into oxazolidinones. Double SN2 mechanism against SN1 mechanism

Sulfonation of the N-Boc derivatives of 1,2-aminoalcohols, such as ephedrine, pseudoephedrine, norephedrine, norpseudoephedrine, thiomicamine, and chloramphenicol yields a mixture of the corresponding oxazolidinones with inversion (erythro derivatives) and!or retention of configuration (threo derivatives)at C5. We suggest a competition between two mechanisms: an intramolecular SN2 process initiated by attack of the carbonyl oxygen of the Boc group to the benzylic carbon and the other one through a double SN2 process. In the erythro derivatives the first mechanism is predominant, while in the threo derivatives both mechanisms have similar energy. This hypothesis is supported by theoretical calculations and additional experimental assays.