25756-06-3

Basic information

• Product Name: 3-amino-1-phenyl-1-butanol
• Synonyms: 3-amino-1-phenyl-1-butanol
• CAS NO: 25756-06-3
• Molecular Weight: 165.235
• Mol File: 25756-06-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 3-amino-1-phenyl-1-butanol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-amino-1-phenyl-1-butanol(25756-06-3)
• EPA Substance Registry System: 3-amino-1-phenyl-1-butanol(25756-06-3)

Safety Data

• Hazardous Substances Data: 25756-06-3(Hazardous Substances Data)

Upstream product

• 55134-78-6 3-methyl-5-phenyl-2-trimethylsilanyloxy-isoxazolidine 
• 7064-06-4 3-methyl-5-phenyl-4,5-dihydroisoxazole 
• 18312-45-3 propan-2-one O-acetyl oxime 
• 100-52-7 benzaldehyde 
• 23652-90-6 3-amino-1-phenylbut-2-en-1-one 
• 56894-87-2 4-acetoxy-4-phenyl-butan-2-one 
• 5381-93-1 1-hydroxy-1-phenyl-3-butanone 
• 753386-78-6 3-Amino-1-phenyl-butan-1-one 
• 95633-12-8 3-benzyloxyimino-1-phenyl-1-butanol 
• 89762-98-1 anti-3-benzyloxyimino-1-phenyl-1-butanol 

Downstream Products

• 73406-38-9 cis-4-methyl-6-phenyltetrahydro-2H-1,3-oxazin-2-one 
• 184303-07-9 [(1-Methyl-3-oxo-3-phenyl-propyl)-(toluene-4-sulfonyl)-amino]-acetic acid benzyl ester 
• 42142-54-1 erythro-3-Methylamino-1-phenyl-butanol 
• 73406-39-0 c-4-Methyl-c-6-phenyl-r-2-(4-nitrophenyl)tetrahydro-1,3-oxazin 

Relevant articles and documents

Selective access to all four diastereomers of a 1,3-amino alcohol by combination of a keto reductase- and an amine transaminase-catalysed reaction

The biocatalytic synthesis of chiral amines has become a valuable addition to the chemists' toolbox. However, the efficient asymmetric synthesis of functionalised amines bearing more than one stereocentre, such as 1,3-amino alcohols, remains challenging. By employing a keto reductase (KRED) and two enantiocomplementary amine transaminases (ATA), we developed a biocatalytic route towards all four diastereomers of 4-amino-1-phenylpentane-2-ol as a representative molecule bearing the 1,3-amino alcohol functionality. Starting from a racemic hydroxy ketone, a kinetic resolution using an (S)-selective KRED provided optically active hydroxy ketone (86% ee) and the corresponding diketone. Further transamination of the hydroxy ketone was performed by either an (R)- or an (S)-selective ATA, yielding the (2R,4R)- and (2R,4S)-1,3-amino alcohol diastereomers. The remaining two diastereomers were accessible in two subsequent asymmetric steps: the diketone was reduced regio- and enantioselectively by the same KRED, which yielded the (S)-configured hydroxy ketone. Eventually, the subsequent transamination of the crude product with (R)- and (S)-selective ATAs yielded the remaining (2S,4R)- and (2S,4S)-diastereomers, respectively.

Generation of chromioenamines by reduction of O-acetyloximes with chromium(II) and their application

Chromioenamines can be generated by treatment of O-acetyloximes with chromium(II) via two steps of one-electron reduction and successive isomerization, and the species react with aldehydes to give γ-amino alcohols after reduction with LiA1H4.

STEREOSELECTIVE PREPARATION OF ACYCLIC syn-1,3-AMINO ALCOHOLS FROM β-HYDROXY KETONES

syn-1,3-Amino alcohols are prepared in good yields by the stereoselective reduction of β-hydroxy-ketone-O-benzyloximes derived from acyclic β-hydroxy ketones with lithium aluminium hydride.