Cyclopropanecarboxamide, 2-[(1S)-1-aminopropyl]-N,N-diethyl-1-phenyl-, (1S,2R)-

Base Information

• Chemical Name: Cyclopropanecarboxamide, 2-[(1S)-1-aminopropyl]-N,N-diethyl-1-phenyl-, (1S,2R)-
• CAS No.: 171889-07-9
• Molecular Formula: C17H26N2O
• Molecular Weight: 274.406
• Mol file: 171889-07-9.mol

Synonyms:

Chemical Property of Cyclopropanecarboxamide, 2-[(1S)-1-aminopropyl]-N,N-diethyl-1-phenyl-, (1S,2R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclopropanecarboxamide, 2-[(1S)-1-aminopropyl]-N,N-diethyl-1-phenyl-, (1S,2R)-

There total 23 articles about Cyclopropanecarboxamide, 2-[(1S)-1-aminopropyl]-N,N-diethyl-1-phenyl-, (1S,2R)- 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: 78.0%

(1S,2R)-2-((S)-1-Amino-allyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide (171889-11-5) → (1S,2R)-1-phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide (171889-07-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 1.5h; under 760 Torr; Ambient temperature;

DOI:10.1021/jm960495w

Reference yield: 74.0%

(1S,2R)-2-((R)-1-Amino-prop-2-ynyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide (779308-86-0) → (1S,2R)-1-phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide (171889-07-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 2h; under 760 Torr; Ambient temperature;

DOI:10.1021/jm980238m

Reference yield:

(1S,2R)-2-Formyl-1-phenyl-cyclopropanecarboxylic acid diethylamide (172016-00-1) → (1S,2R)-1-phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide (171889-07-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93 percent / molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 20 °C

2.1: MgBr₂ / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C

2.2: 80 percent / diethyl ether; tetrahydrofuran / 8 h / -78 °C

3.1: H₂ / 10percent Pd/C / methanol / 72 h / 1551.49 Torr

With 4 A molecular sieve; hydrogen; magnesium bromide; 10percent Pd/C; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1039/b008230i

upstream raw materials:

(1S,2R)-1-phenyl-2-<(S)-1-azidopropyl>-N,N-diethylcyclopropanecarboxamide

(1S,2R)-2-((S)-1-Amino-allyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide

(1S,2R)-2-((R)-1-Amino-prop-2-ynyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide

(1S,2R)-1-Phenyl-2-[(S)-1-(N-benzyl-N-hydroxyamino)propyl]-N,N-diethylcyclopropanecarboxamide

Downstream raw materials:

[(S)-1-((1R,2S)-2-Diethylcarbamoyl-2-phenyl-cyclopropyl)-propyl]-methyl-carbamic acid tert-butyl ester

(1S,2R)-1-phenyl-2-[(S)-1-tert-butoxycarbonylaminopropyl]-N,N-diethylcyclopropanecarboxamide

Refernces

• 1、 Shuto, Satoshi,Ono, Shizuka,Imoto, Hiroaki,Yoshii, Kiyonori,Matsuda, Akira. "Synthesis and biological activity of conformationally restricted analogues of milnacipran: (1S,2R)-1-phenyl-2-[(R)-1-amino-2-propynyl]-N,N- diethylcyclopropanecarboxamide is a novel class of NMDA receptor channel blocker". . p. 3507 - 3514. Retrieved 2007/10/03.
• 2、 Shuto, Satoshi,Ono, Shizuka,Hase, Yukako,Ueno, Yoshihito,Noguchi, Tomohiro,Yoshii, Kiyonori,Matsuda, Akira. "Synthesis and biological activity of conformationally restricted analogs of milnacipran: (1S,2A)-1-Phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide, an efficient noncompetitive N-methyl-D-aspartic acid receptor antagonist". . p. 4844 - 4852. Retrieved 2007/10/03.