(S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile

Base Information

• Chemical Name: (S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile
• CAS No.: 225918-54-7
• Molecular Formula: C₂₁H₁₇ClN₂
• Molecular Weight: 332.832
• Mol file: 225918-54-7.mol

Synonyms:(S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile

Chemical Property of (S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile

There total 5 articles about (S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

trimethylsilyl cyanide (7677-24-9) + N-(2-chlorobenzylidene)-1,1-diphenylmethanamine (69790-43-8) → (S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile (225918-54-7)

Guidance literature:

With titanium(IV) isopropylate; isopropyl alcohol; N-(2'-hydroxyphenyl)methyl-(S)-2-amino-3-phenyl-propan-1-ol; In toluene; at 0 ℃; for 72h; optical yield given as %ee; enantioselective reaction;

DOI:10.1016/j.tet.2009.04.098

Reference yield: 85.0%

trimethylsilyl cyanide (7677-24-9) + N-benzyhydryl-(2-chlorobenzylidene)-amine (387845-99-0) → (S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile (225918-54-7)

Guidance literature:

With titanium(IV) isopropylate; C₂₄H₃₅Cl₂N₃O₆; isopropyl alcohol; In toluene; at 4 ℃; for 20h;

DOI:10.1021/ja9840605

Reference yield:

trimethylsilyl cyanide (7677-24-9) + N-(2-chlorobenzylidene)-1,1-diphenylmethanamine (69790-43-8) → (S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile (225918-54-7) + (R)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile

Guidance literature:

N-(2-chlorobenzylidene)-1,1-diphenylmethanamine; With self-assembled organic-inorganic hybrid silica with ionic liquid phase supported ytterbium(III) triflate-(4-bromo-2,6-bis-(4-phenyloxazol-2-yl)-pyridine) complex; In dichloromethane; at -40 ℃; for 0.333333h; Inert atmosphere;

trimethylsilyl cyanide; In methanol; dichloromethane; at -40 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1039/c0cc01426e

upstream raw materials:

trimethylsilyl cyanide

N-benzyhydryl-(2-chlorobenzylidene)-amine

N-(2-chlorobenzylidene)-1,1-diphenylmethanamine

2-chloro-benzaldehyde

Downstream raw materials:

(2S)-2-(2-chlorophenyl)glycine hydrochloride

N-Boc-(S)-2-chlorophenylglycine

(S)-2-amino-(2-chlorophenyl)ethanoic acid

Refernces

• 1、 Seayad, Abdul M.,Ramalingam, Balamurugan,Chai, Christina L. L.,Li, Chuanzhao,Garland, Marc V.,Yoshinaga, Kazuhiko. "Self-supported chiral titanium cluster (SCTC) as a robust catalyst for the asymmetric cyanation of imines under batch and continuous flow at room temperature". supporting information; experimental part. p. 5693 - 5700. Retrieved 2012/06/15.
• 2、 Seayad, Abdul Majeed,Ramalingam, Balamurugan,Yoshinaga, Kazuhiko,Nagata, Takushi,Chai, Christina L. L.. "Highly enantioselective titanium-catalyzed cyanation of imines at room temperature". supporting information; experimental part. p. 264 - 267. Retrieved 2010/03/24.