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

Base Information

• Chemical Name: (1S,2R)-1-phenyl-2-<(S)-1-azidoethyl>-N,N-diethylcyclopropanecarboxamide
• CAS No.: 171889-15-9
• Molecular Formula: C₁₆H₂₂N₄O
• Molecular Weight: 286.377
• Mol file: 171889-15-9.mol

Synonyms:(1S,2R)-1-phenyl-2-<(S)-1-azidoethyl>-N,N-diethylcyclopropanecarboxamide

Chemical Property of (1S,2R)-1-phenyl-2-<(S)-1-azidoethyl>-N,N-diethylcyclopropanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-1-phenyl-2-<(S)-1-azidoethyl>-N,N-diethylcyclopropanecarboxamide

There total 7 articles about (1S,2R)-1-phenyl-2-<(S)-1-azidoethyl>-N,N-diethylcyclopropanecarboxamide 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: 62.0%

(1S,2R)-1-phenyl-2-<(S)-1-hydroxyethyl>-N,N-diethylcyclopropanecarboxamide (171889-13-7) → (1S,2R)-1-phenyl-2-<(S)-1-azidoethyl>-N,N-diethylcyclopropanecarboxamide (171889-15-9)

Guidance literature:

With sodium azide; carbon tetrabromide; triphenylphosphine; In N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(95)02221-X

Reference yield:

(1 S,2 R)-N,N-diethyl-2-(hydroxymethyl)-1-phenylcyclopropane-carboxamide (172015-99-5) → (1S,2R)-1-phenyl-2-<(S)-1-azidoethyl>-N,N-diethylcyclopropanecarboxamide (171889-15-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 2 h; 2) CH₂Cl₂, -78 deg C, 1 h

2: 93 percent / tetrahydrofuran / 2 h / -20 °C

3: 62 percent / NaN₃, Ph₃P, CBr₄ / dimethylformamide / 3 h / Ambient temperature

With sodium azide; oxalyl dichloride; carbon tetrabromide; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo9518056

Reference yield:

(1S,2R)-2-Formyl-1-phenyl-cyclopropanecarboxylic acid diethylamide (172016-00-1) → (1S,2R)-1-phenyl-2-<(S)-1-azidoethyl>-N,N-diethylcyclopropanecarboxamide (171889-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / tetrahydrofuran / 2 h / -20 °C

2: 62 percent / NaN₃, Ph₃P, CBr₄ / dimethylformamide / 3 h / Ambient temperature

With sodium azide; carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo9518056

upstream raw materials:

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

Trifluoro-acetic acid (S)-1-((1R,2S)-2-diethylcarbamoyl-2-phenyl-cyclopropyl)-ethyl ester

1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

(1 S,2 R)-N,N-diethyl-2-(hydroxymethyl)-1-phenylcyclopropane-carboxamide

Downstream raw materials:

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