160194-14-9

Basic information

• Product Name: 2-Benzylamino-4-chloro-3,3-dimethyl-butyric acid methyl ester
• Synonyms: 2-Benzylamino-4-chloro-3,3-dimethyl-butyric acid methyl ester
• CAS NO: 160194-14-9
• Molecular Weight: 269.771
• Mol File: 160194-14-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-Benzylamino-4-chloro-3,3-dimethyl-butyric acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzylamino-4-chloro-3,3-dimethyl-butyric acid methyl ester(160194-14-9)
• EPA Substance Registry System: 2-Benzylamino-4-chloro-3,3-dimethyl-butyric acid methyl ester(160194-14-9)

Safety Data

• Hazardous Substances Data: 160194-14-9(Hazardous Substances Data)

Upstream product

• 146679-16-5 4-Chloro-3,3-dimethyl-2-oxo-butyric acid methyl ester 
• 100-46-9 benzylamine 
• 146446-29-9 1,1-dibromo-4-chloro-3,3-dimethyl-2-butanone 
• 160193-96-4 1,1,4-Trichloro-1-(1-chloro-ethylsulfanyl)-3,3-dimethyl-butan-2-one 
• 160193-99-7 4-Chloro-1,1,1-trimethoxy-3,3-dimethyl-2-butanone 
• 146679-15-4 1,1,4-trichloro-1-(phenylthio)-3,3,-dimethyl-2-butanone 
• 146679-14-3 1,1,4-trichloro-1-(ethylthio)-3,3,-dimethyl-2-butanone 
• 146679-12-1 4-chloro-1-(ethylthio)-3,3-dimethyl-2-butanone 
• 13104-53-5 4-chloro-3,3-dimethylbutane-2-one 
• 24706-87-4 2,2-Dimethyl-3-oxo-1-butyl trifluoroacetate 
• 4301-02-4 3,3-dimethyl-4-[(methylsulphonyl)oxy]-2-butanone 
• 1823-90-1 4-hydroxy-3,3-dimethyl-butan-2-one 
• 563-80-4 3-methyl-butan-2-one 
• 160194-05-8 2-[(Z)-Benzylimino]-4-chloro-3,3-dimethyl-butyric acid methyl ester 

Downstream Products

• 160194-12-7 Methyl 1-(N-benzylamino)-2,2-dimethylcyclopropanecarboxylic ester 

Relevant articles and documents

Synthesis of 3,3-dimethylazetidine-2-carboxylic acid and some derivatives

γ-Chloro-α-(N-alkylimino)esters were reduced by sodium cyanoborohydride in methanol in the presence of acetic acid with complete selectivity to give rise to either γ-chloro-α-(N-alkylamino)esters (reaction at 0°C) or 1-alkyl-3,3-dimethylazetidine-2-carboxylic esters (reaction at reflux). The isolable γ-chloro-α-(N-alkylamino)esters are suitable sources for I-(N-alkylamino)-2,2-dimethylcyclopropane-1-carboxylic esters via base-induced 1,3-dehydrochlorination, while the former substrates as transient species undergo 1,4-dehydrochlorination to the corresponding azetidines. The latter process was used for the synthesis of 3,3-dimethylazetidine-2-carboxylic acid, a new non-proteinogenic sterically hindered α-amino acid, via hydrogenolysis of methyl 1-benzyl-3,3-dimethylazetidine-1-carboxylate and subsequent acidic hydrolysis. Reduction of alkyl 4-chloro-3,3-dimethyl-α-(N-alkylimino)butanoates with lithiumaluminiumhydride in diethyl ether afforded 1-alkyl-3,3-dimethyl-2-(hydroxymethyl)-azetidines.