(1S,2S)-1-(N-diphenylmethyleneamino)-2-ethylcyclopropanecarbonitrile

Base Information

• Chemical Name: (1S,2S)-1-(N-diphenylmethyleneamino)-2-ethylcyclopropanecarbonitrile
• CAS No.: 161449-58-7
• Molecular Formula: C₁₉H₁₈N₂
• Molecular Weight: 274.365
• Mol file: 161449-58-7.mol

Synonyms:(1S,2S)-1-(N-diphenylmethyleneamino)-2-ethylcyclopropanecarbonitrile

Chemical Property of (1S,2S)-1-(N-diphenylmethyleneamino)-2-ethylcyclopropanecarbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S)-1-(N-diphenylmethyleneamino)-2-ethylcyclopropanecarbonitrile

There total 11 articles about (1S,2S)-1-(N-diphenylmethyleneamino)-2-ethylcyclopropanecarbonitrile 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: 65.0%

(3R)-3-(chloromethyl)-2-(diphenylmethyleneamino)valeronitrile → (1S,2S)-1-(N-diphenylmethyleneamino)-2-ethylcyclopropanecarbonitrile (161449-58-7) + (1R,2S)-1-(diphenylmethyleneamino)-2-ethylcyclopropanecarbonitrile (161512-80-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -90 ℃; for 3h;

Reference yield:

2-ethyl-1,3-propandiol (2612-29-5) → (1S,2S)-1-(N-diphenylmethyleneamino)-2-ethylcyclopropanecarbonitrile (161449-58-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / diisopropyl ether / 1 h / Ambient temperature; lipase Pseudomonas cepacia

2: 2 M NaOH / Ambient temperature; lipase Pseudomonas cepacia, pH=7.2

3: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, -70 deg C to RT

4: 1.) RT, 1 h, 2.) MeOH, reflux, 8 h

5: 54 percent / K₂CO₃ / 2 h / Ambient temperature

6: 92 percent / Et₃N, 2,4-dimethylaminopyridine / CH₂Cl₂ / 4 h / 0 °C

7: 93 percent / LiCl / various solvent(s) / Ambient temperature

8: 1.) RuCl₂(PPh₃)2, 4 A molecular sieves, 2.) tert-butylperoxide / 1.) C₆H₆, 5 min, 2.) C₆H₆, 0 deg C, 15 h

9: 65 percent / K₂CO₃ / dimethylformamide / 3 h

With sodium hydroxide; ruthenium(II) bis(triphenylphosphine) dichloride; oxalyl dichloride; di-tert-butyl peroxide; 2,4-dimethylaminopyridine; 4 A molecular sieve; potassium carbonate; dimethyl sulfoxide; triethylamine; lithium chloride; In dichloromethane; di-isopropyl ether; N,N-dimethyl-formamide;

Reference yield:

ethyl diethyl malonate (133-13-1) → (1S,2S)-1-(N-diphenylmethyleneamino)-2-ethylcyclopropanecarbonitrile (161449-58-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 80 percent / LiAlH₄ / diethyl ether / 1.5 h / Ambient temperature

2: 80 percent / diisopropyl ether / 1 h / Ambient temperature; lipase Pseudomonas cepacia

3: 2 M NaOH / Ambient temperature; lipase Pseudomonas cepacia, pH=7.2

4: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, -70 deg C to RT

5: 1.) RT, 1 h, 2.) MeOH, reflux, 8 h

6: 54 percent / K₂CO₃ / 2 h / Ambient temperature

7: 92 percent / Et₃N, 2,4-dimethylaminopyridine / CH₂Cl₂ / 4 h / 0 °C

8: 93 percent / LiCl / various solvent(s) / Ambient temperature

9: 1.) RuCl₂(PPh₃)2, 4 A molecular sieves, 2.) tert-butylperoxide / 1.) C₆H₆, 5 min, 2.) C₆H₆, 0 deg C, 15 h

10: 65 percent / K₂CO₃ / dimethylformamide / 3 h

With sodium hydroxide; lithium aluminium tetrahydride; ruthenium(II) bis(triphenylphosphine) dichloride; oxalyl dichloride; di-tert-butyl peroxide; 2,4-dimethylaminopyridine; 4 A molecular sieve; potassium carbonate; dimethyl sulfoxide; triethylamine; lithium chloride; In diethyl ether; dichloromethane; di-isopropyl ether; N,N-dimethyl-formamide;

upstream raw materials:

2-ethyl-1,3-propandiol

1,3-di-O-acetyl-2-ethyl-1,3-propanediol

(R)-1-O-acetyl-2-ethyl-1,3-propanediol

ethyl diethyl malonate

Downstream raw materials:

(-)-(1R,2R)-coronamic acid

(1S,2S)-(+)-1-Amino-2-ethyl-1-cyclopropanecarboxylic Acid

Refernces

• 1、 Gaucher, Anne,Ollivier, Jean,Marguerite, Jacqueline,Paugam, Renee,Salauen, Jacques. "Total asymmetric syntheses of (1S,2S)-norcoronamic acid, and of (1R,2R)- and (1S,2S)-coronamic acids from the diastereoselective cyclization of 2-(N-benzylideneamino)-4-chlorobutyronitriles". . p. 1312 - 1327. Retrieved 2007/10/02.