(1S,2R)-2-[(1S)-1-[benzyl(hydroxy)amino]ethyl]-N,N-diethyl-1-phenylcyclopropane-1-carboxamide

Base Information

• Chemical Name: (1S,2R)-2-[(1S)-1-[benzyl(hydroxy)amino]ethyl]-N,N-diethyl-1-phenylcyclopropane-1-carboxamide
• CAS No.: 288627-97-4
• Molecular Formula: C₂₃H₃₀N₂O₂
• Molecular Weight: 366.503
• DSSTox Substance ID: DTXSID601116377
• Nikkaji Number: J1.357.169D
• Mol file: 288627-97-4.mol

Synonyms:DTXSID601116377;288627-97-4;(1S,2R)-N,N-Diethyl-2-[(1S)-1-[hydroxy(phenylmethyl)amino]ethyl]-1-phenylcyclopropanecarboxamide

Chemical Property of (1S,2R)-2-[(1S)-1-[benzyl(hydroxy)amino]ethyl]-N,N-diethyl-1-phenylcyclopropane-1-carboxamide

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 366.230728204
• Heavy Atom Count: 27
• Complexity: 481

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCN(CC)C(=O)C1(CC1C(C)N(CC2=CC=CC=C2)O)C3=CC=CC=C3
• Isomeric SMILES: CCN(CC)C(=O)[C@]1(C[C@H]1[C@H](C)N(CC2=CC=CC=C2)O)C3=CC=CC=C3

Technology Process of (1S,2R)-2-[(1S)-1-[benzyl(hydroxy)amino]ethyl]-N,N-diethyl-1-phenylcyclopropane-1-carboxamide

There total 5 articles about (1S,2R)-2-[(1S)-1-[benzyl(hydroxy)amino]ethyl]-N,N-diethyl-1-phenylcyclopropane-1-carboxamide 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: 81.0%

methylmagnesium bromide (75-16-1) + N-[(1R,2S)-2-(N,N-Diethylcarbamoyl)-2-phenylcyclopropylmethylene]benzylamine N-oxide (350507-27-6,288627-96-3) → (1S,2R)-1-Phenyl-2-[(S)-1-(N-benzyl-N-hydroxyamino)ethyl]-N,N-diethylcyclopropanecarboxamide (288627-97-4)

Guidance literature:

With magnesium bromide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 8h;

DOI:10.1016/S0040-4039(00)00823-6

Reference yield: 80.0%

methylmagnesium bromide (75-16-1) + N-[(1R,2S)-2-(N,N-Diethylcarbamoyl)-2-phenylcyclopropylmethylene]benzylamine N-oxide (350507-27-6,288627-96-3) → (1S,2R)-1-Phenyl-2-[(S)-1-(N-benzyl-N-hydroxyamino)ethyl]-N,N-diethylcyclopropanecarboxamide (288627-97-4) + (1S,2R)-1-Phenyl-2-[(R)-1-(N-benzyl-N-hydroxyamino)ethyl]-N,N-diethylcyclopropanecarboxamide

Guidance literature:

N-[(1R,2S)-2-(N,N-Diethylcarbamoyl)-2-phenylcyclopropylmethylene]benzylamine N-oxide; With magnesium bromide; In tetrahydrofuran; diethyl ether; at 20 ℃; for 0.5h;

methylmagnesium bromide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 8h;

DOI:10.1039/b008230i

Reference yield:

(1S,2R)-2-Formyl-1-phenyl-cyclopropanecarboxylic acid diethylamide (172016-00-1) → (1S,2R)-1-Phenyl-2-[(S)-1-(N-benzyl-N-hydroxyamino)ethyl]-N,N-diethylcyclopropanecarboxamide (288627-97-4)

Guidance literature:

Multi-step reaction with 2 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

With 4 A molecular sieve; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1039/b008230i

upstream raw materials:

methylmagnesium bromide

N-[(1R,2S)-2-(N,N-Diethylcarbamoyl)-2-phenylcyclopropylmethylene]benzylamine N-oxide

N-benzylhydroxylamine hydrochloride

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

Downstream raw materials:

1-phenyl-2-[(S)-1-aminoethyl]-N,N-diethylcyclopropanecarboxamide