199392-90-0

Basic information

• Product Name: [(S)-1-(4-Fluoro-phenyl)-2-hydroxy-ethyl]-carbamic acid benzyl ester
• Synonyms: [(S)-1-(4-Fluoro-phenyl)-2-hydroxy-ethyl]-carbamic acid benzyl ester
• CAS NO: 199392-90-0
• Molecular Weight: 289.306
• Mol File: 199392-90-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: [(S)-1-(4-Fluoro-phenyl)-2-hydroxy-ethyl]-carbamic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [(S)-1-(4-Fluoro-phenyl)-2-hydroxy-ethyl]-carbamic acid benzyl ester(199392-90-0)
• EPA Substance Registry System: [(S)-1-(4-Fluoro-phenyl)-2-hydroxy-ethyl]-carbamic acid benzyl ester(199392-90-0)

Safety Data

• Hazardous Substances Data: 199392-90-0(Hazardous Substances Data)

Upstream product

• 405-99-2 para-fluorostyrene 
• 621-84-1 O-benzyl carbamate 
• 224433-80-1 [(S)-1-(4-Fluoro-phenyl)-2-((R)-toluene-4-sulfinyl)-ethyl]-(4-methoxy-phenyl)-amine 
• 501-53-1 benzyl chloroformate 
• 130632-07-4 (E)-1-(4-fluorophenyl)-N-(4-methoxyphenyl)methanimine 
• 459-57-4 4-fluorobenzaldehyde 
• 224433-97-0 [(S)-1-(4-Fluoro-phenyl)-2-((R)-toluene-4-sulfinyl)-ethyl]-carbamic acid benzyl ester 
• 224433-93-6 (S)-1-(4-Fluoro-phenyl)-2-((R)-toluene-4-sulfinyl)-ethylamine 

Downstream Products

• 224434-01-9 (S)-1-(4-fluorophenyl)-2-hydroxyethylamine 

Relevant articles and documents

Asymmetric synthesis of α-arylglycinols via additions of lithium methyl p-tolyl sulfoxide to N-(PMP)arylaldimines followed by 'non oxidative' Pummerer reaction

The results presented in this paper demonstrate that the stereochemical outcome of the reversible additions of lithium (R)-methyl p-tolyl sulfoxide to N-arylidene-p-anisidines (N-PMP imines) is a function of a) the reaction conditions used and b) the electronic properties of the arylidene moiety on the starting imine. High kinetically controlled (2S,R(S)) diastereoselectivity (-70 °C) was achieved for additions of imines bearing relatively electron-rich N-arylidene groups, while an electron-deficient nature of this group was found to favor the opposite stereochemical outcome. On the other hand, the reactions run under thermodynamically controlled conditions (0 °C) afforded equimolar mixtures of the diastereomeric products regardless of the pattern of substitution on the starting imines. Enantiopure α-arylglycinols were readily synthesized by 'non-oxidative' Pummerer rearrangement of diastereomerically pure β-aryl-β-N-(acyl)aminoalkyl sulfoxides, prepared from the corresponding N-PMP derivatives.