105370-59-0

Basic information

• Product Name: Benzenemethanamine, a-butyl-, (R)-
• CAS NO: 105370-59-0
• Molecular Formula: C11H17N
• Molecular Weight: 163.263
• Mol File: 105370-59-0.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: Benzenemethanamine, a-butyl-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanamine, a-butyl-, (R)-(105370-59-0)
• EPA Substance Registry System: Benzenemethanamine, a-butyl-, (R)-(105370-59-0)

Safety Data

• Hazardous Substances Data: 105370-59-0(Hazardous Substances Data)

Upstream product

• 131214-10-3 (2R,1'R)-2-<(1'-phenylpentyl)amino>-2-phenylethanol 
• 131154-13-7 4-Methyl-benzenesulfinic acid ((R)-1-phenyl-pentyl)-amide 
• 109-72-8 n-butyllithium 
• 100-47-0 benzonitrile 
• 862776-58-7 (S)-N-benzylidene-2-methylpropane-2-sulfinamide 
• 911372-70-8 (R_S)-2-methyl-N-((R)-1-phenylpentyl)propane-2-sulfinamide 
• 100-52-7 benzaldehyde 
• 131154-12-6 4-Methyl-benzenesulfinic acid [1-phenyl-pent-(E)-ylidene]-amide 
• 249920-08-9 2,4-diphenyl-1,3-oxazolidine 
• 321-97-1 (1R,2R)-pseudoephedrine 
• 122-56-5 tributyl borane 
• 120419-97-8 (E)-N-benzylidene-1,1,1-trimethylsilanamine 

Downstream Products

• 1106777-28-9 (R)-N-(1-phenylpentyl)benzamide 

Relevant articles and documents

Asymmetric Addition of Butyllithium to N-Metallo Imines of Benzaldehyde

N-Metallo imines derived from benzaldehyde such as N-aluminium imine, N-boryl imine and N-silyl imine were asymmetrically alkylated with butyllithium in the presence of chiral ligands including (-)-sparteine and proline-derived amino alcohols to give optically active 1-phenylpentyl-1-amine in up to 74percent anantiomeric excess.Polymer-supported chiral ligands were also used for the asymmetric addition.

Addition of Highly Polarized Organometallic Compounds to N-tert-Butanesulfinyl Imines in Deep Eutectic Solvents under Air: Preparation of Chiral Amines of Pharmaceutical Interest

Highly polarized organometallic compounds of s-block elements are added smoothly to chiral N-tert-butanesulfinyl imines in the biodegradable d-sorbitol/choline chloride eutectic mixture, thereby granting access to enantioenriched primary amines after quantitatively removing the sulfinyl group. The practicality of the method is further highlighted by proceeding at ambient temperature and under air, with very short reaction times (2 min), enabling the preparation of diastereoisomeric sulfinamides in very good yields (74–98 %) and with a broad substrate scope, and the possibility of scaling up the process. The method is demonstrated in the asymmetric syntheses of both the chiral amine side-chain of (R,R)-Formoterol (96 % ee) and the pharmaceutically relevant (R)-Cinacalcet (98 % ee).

Studies on the bisoxazoline- and (-)-sparteine-mediated enantioselective addition of organolithium reagents to imines

The enantioselective addition of organolithium reagents to N-anisylaldimines promoted by chiral bisoxazolines and (-)-sparteine as external ligands is described. This reaction proceeds readily with a wide range of aldimine substrates (aliphatic, aromatic, olefinic) and organolithium nucleophiles (Me, n-Bu, Ph, vinyl) in excellent yields (81-99%) and with high enantioselectivities (up to 97:3.0 er). The external ligands can be used in substoichiometric amounts albeit with slightly attenuated enantioselectivities. A systematic evaluation of the structural features of the bisoxazolines revealed a primary contribution from the substituent at C(4) and a secondary influence from the bridging substituents. A computational analysis (PM3) provided a clear rationalization for the origin of enantioselectivity.

β-Silylated homopropargylic amines via the asymmetric allenylboration of aldimines

(Chemical Equation Presented) The asymmetric synthesis of α-trimethylsilylpropargylic carbamines (7) through the addition of allenylboranes 4 to N-H aldimines is reported. The insertion of TMSCHN 2 into enantiomerically pure B-alkynyl-10-TMS-9-