126927-38-6

Basic information

• Product Name: (1S,1'S)-N-2'-hydroxy-1'-phenylethyl-1-phenylethylamine
• Synonyms: (1S,1'S)-N-2'-hydroxy-1'-phenylethyl-1-phenylethylamine
• CAS NO: 126927-38-6
• Molecular Weight: 241.333
• Mol File: 126927-38-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1S,1'S)-N-2'-hydroxy-1'-phenylethyl-1-phenylethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,1'S)-N-2'-hydroxy-1'-phenylethyl-1-phenylethylamine(126927-38-6)
• EPA Substance Registry System: (1S,1'S)-N-2'-hydroxy-1'-phenylethyl-1-phenylethylamine(126927-38-6)

Safety Data

• Hazardous Substances Data: 126927-38-6(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 69350-13-6 N-benzylidene-(S)-α-methylbenzylamine 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 132273-97-3 (S)-N-1'-phenyl-1'-ethoxycarbonylmethylidene-1-phenylethylamine 
• 15028-39-4 L-2-phenylglycine methyl ester hydrochloride 
• 127001-23-4 (+)-(S)-2-(phenylmethoxy)-N-<(2-chlorobenzoyl)oxy>-1-phenylethanamine 
• 127001-23-4 (+/-)-2-(phenylmethoxy)-N-<(2-chlorobenzoyl)oxy>-1-phenylethanamine 
• 127001-25-6 (-)-(S)-N-benzylidene-2-(phenylmethoxy)-1-phenylethanamine N-oxide 
• 126927-07-9 N-<2'-(phenylmethoxy)-1'-phenylethyl>-N-hydroxy-1-phenylethanamine 
• 126927-02-4 (+)-(S)-N-hydroxy-2-(phenylmethoxy)-1-phenylethanamine 
• 127001-24-5 (+/-)-N-hydroxy-2-(phenylmethoxy)-1-phenylethanamine 
• 127001-22-3 (S)-1-phenyl-2-(phenylmethoxy)ethylamine 
• 127001-22-3 (+/-)-phenylglycinol benzyl ether 

Downstream Products

• 20989-17-7 (2S)-2-phenylglycinol 
• 126927-40-0 (1'R*,1R*)-N-(2'-methoxy-1'-phenylethyl)-N-methyl-1-phenylethanamine 
• 90933-77-0 N-(2'-methoxy-1'-phenylethyl)-1-phenylethanamine 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Relevant articles and documents

Synthesis of 1,2-aminoalcohols by Ti(IV)-catalyzed photohydroxymethylation of chiral aldimines

The N-(α-phenylethyl) alkylated aldimines 3a-c are conveniently hydroxymethylated with moderate diastereoselectivities by means of irradiation in methanolic solution in the presence of titanium(IV)chloride.

Enantioselective Synthesis of Primary Amines via Grignard Additions to Stereogenic N-(α-Phenyl-β-(benzyloxy)ethyl)nitrones

Addition of a wide range of Grignard to C-aryl- and C-alkyl-N-(α-phenyl-β-(benzyloxy)ethyl)nitrones (4-7) occurred with high diastereoselectivity (90:10 to 97:3 ratios) and good yields (56 - 97percent).Notable exceptions are allyl- and (o-methoxyphenyl)magnesium bromides (low selectivity but satisfactory yields) and isopropyl- and tert-butylmagnesium chlorides (high selectivity but 33 - 34percent yields) with C-phenylnitrone 4.The relative stereochemistry of hydroxylamine adducts 8a,b (from reaction of 4 with CH3MgBr) and 19a,b (from C-pentylnitrone 7 with MeMgBr) was provenby various correlations and/or by degradation to enantiomerically enriched amines.The other stereochemical assignments are based upon 1H NMR spectral and polarity correlations and/or by analogy to the two proven cases.The configuration of the major product can be rationalized by assuming that the Grignard reagents attack the nitrone face opposite to the pseudoequatorial N-(α-phenyl) group in a six-membered magnesium chelate (27 -> 28). 1H NMR spectral evidence indicates that a 1:1 complex of nitrone 4 and magnesium bromide exists in a chelated structure (29B) in CD2Cl2.Enantioselective syntheses of (S)-α-phenylethylamine (94percent ee) and (S)-2-heptylamine (82percent ee) were accomplished in five steps (33-39percent overall yields) from optically pure (S)-nitrones 4 and 7.