107381-30-6

Basic information

• Product Name: hydrocinnamaldehyde SAMP-hydrazone
• Synonyms: hydrocinnamaldehyde SAMP-hydrazone
• CAS NO: 107381-30-6
• Molecular Weight: 246.352
• Mol File: 107381-30-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: hydrocinnamaldehyde SAMP-hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: hydrocinnamaldehyde SAMP-hydrazone(107381-30-6)
• EPA Substance Registry System: hydrocinnamaldehyde SAMP-hydrazone(107381-30-6)

Safety Data

• Hazardous Substances Data: 107381-30-6(Hazardous Substances Data)

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 59983-39-0 (S)-1-amino-2-(methoxymethyl)pyrrolidine 

Downstream Products

• 937-52-0 (R)-1-methyl-3-phenylpropylamine 
• 107300-30-1 ((S)-2-Methoxymethyl-pyrrolidin-1-yl)-((E)-(R)-1-phenethyl-3-triisopropylsilanyl-allyl)-carbamic acid methyl ester 
• 107300-27-6 (2S,2''S)-1-[N-(1-(1-methylethyl)-3-phenylpropyl)-N-methoxycarbonylamino]-2-(methoxymethyl)pyrrolidine 
• 127222-05-3 ((S)-2,2-Dimethyl-1-phenethyl-propyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-carbamic acid methyl ester 
• 107300-18-5 (2S,2''R)-1-[N-methoxycarbonyl-N-(1-methyl-3-phenylpropyl)amino]-2-(methoxymethyl)pyrrolidine 
• 107300-26-5 ((S)-2-Methoxymethyl-pyrrolidin-1-yl)-((R)-1-phenethyl-pentyl)-carbamic acid methyl ester 
• 107300-29-8 (2S,2''S)-1-[N-(1',3'-diphenylpropyl)-N-methoxycarbonylamino]-2-methoxymethylpyrrolidine 

Relevant articles and documents

Asymmetric synthesis of β-substituted γ-lactams employing the samp-/ramp-hydrazone methodology. Application to the synthesis of (R-(-)-baclofen

A short and efficient asymmetric synthesis of β-substituted γ-lactams is described. Key steps are the α-alkylation of aldehyde SAMP-hydrazones with alkyl bromoacetates, their MMPP mediated conversion to the corresponding nitriles and a reductive cyclization with Raney Ni or Ni boride to the title pyrrolidin-2-ones. The β-substituted γ-lactams are obtained in three steps, good overall yields (27-78%) and excellent enantiomeric excesses (ee=93-99%). The applicability of this procedure for the asymmetric synthesis of GABAs (γ-aminobutyric acids) is demonstrated for (R-(-)-baclofen hydrochloride, which is obtained in 4 steps 55% yield and 94% ee.