148065-58-1

Basic information

• Product Name: *,S^*)>-α-methyl-N-(1-phenylethyl)benzenepropanamide
• Synonyms: *,S^*)>-α-methyl-N-(1-phenylethyl)benzenepropanamide
• CAS NO: 148065-58-1
• Molecular Weight: 253.387
• Mol File: 148065-58-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: *,S^*)>-α-methyl-N-(1-phenylethyl)benzenepropanamide(CAS DataBase Reference)
• NIST Chemistry Reference: *,S^*)>-α-methyl-N-(1-phenylethyl)benzenepropanamide(148065-58-1)
• EPA Substance Registry System: *,S^*)>-α-methyl-N-(1-phenylethyl)benzenepropanamide(148065-58-1)

Safety Data

• Hazardous Substances Data: 148065-58-1(Hazardous Substances Data)

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 130562-15-1 [1-(2-Fluoro-phenyl)-eth-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine 
• 2550-26-7 4-Phenyl-2-butanone 

Downstream Products

• 81580-38-3 (S)-2-hydroxy-5-<acetyl>benzamide 
• 83167-31-1 *)>-2-hydroxy-5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)amino>ethyl>benzamide 
• 83167-24-2 *)>-2-hydroxy-5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)amino>ethyl>benzamide 
• 75659-04-0 (-)-(S)-α-methyl-N-(phenylmethyl)benzenepropanamine 
• 4187-36-4 ((S)-1-Methyl-3-phenyl-propyl)-[1-phenyl-meth-(E)-ylidene]-amine 
• 4187-57-9 (S)-1-methyl-3-phenylpropylamine 

Relevant articles and documents

B(C6F5)3-Catalyzed Asymmetric Reductive Amination of Ketones with Ammonia Borane

The first example of metal-free B(C6F5)3-catalyzed asymmetric reduction amination of ketones with chiral α-methylbenzylamine (α-MBA) using ammonia borane as the reductant is reported. This one-pot method has a broad substrate scope and provides various chiral amines in 81-95% yield with 80-99% de. This protocol was further applied in the total synthesis of cinacalcet.

Ytterbium acetate promoted asymmetric reductive amination: Significantly enhanced stereoselectivity

(Chemical Equation Presented) Reductive amination of prochiral unhindered 2-alkanones 1 with (R)- or (S)-α-MBA in the presence of Yb(OAc) 3 (50-110 mol %), Raney-Ni, and hydrogen (120 psi) results in increased diastereoselectivity for the amine products 2 (80-89% de) with good yield (80-87%). The increased de is based on comparison with the best previously reported de's when using (R)- or (S)-α-MBA, regardless of the strategy employed [stepwise (isolation of ketimines) or one-pot (reductive amination)], reducing agent examined, or achiral Lewis acid or Bronsted acid examined. An in situ cis- to trans-ketimine isomerization mechanism, promoted by Yb(OAc)3, has been proposed to account for the observed increase in diastereoselectivity and suggests a new entry into the control of ketimine geometry.

SYNTHESIS OF AMINES WITH CATALYTIC AMOUNTS OF MILD LEWIS ACIDS

The invention relates to methods for producing primary, secondary and tertiary amines and corresponding enantiopure or enantioenriched primary or secondary amine products, comprising the steps of reductively aminating a ketone, with a nitrogen auxiliary in the presence of a hydrogenating catalyst and a hydrogenating agent, wherein the reductive animation is performed under the influence of a mild Lewis acid, the mild Lewis acid being present at the onset of the reductive amination in at most 25 mol% of the ketone or the nitrogen auxiliary.