(1S,2R)-1-phenyl-2-[(S)-1-azidopropyl]-N,N-di-isobutylcyclopropanecarboxamide

Base Information

• Chemical Name: (1S,2R)-1-phenyl-2-[(S)-1-azidopropyl]-N,N-di-isobutylcyclopropanecarboxamide
• CAS No.: 459143-54-5
• Molecular Formula: C₂₁H₃₂N₄O
• Molecular Weight: 356.511
• Mol file: 459143-54-5.mol

Synonyms:(1S,2R)-1-phenyl-2-[(S)-1-azidopropyl]-N,N-di-isobutylcyclopropanecarboxamide

Chemical Property of (1S,2R)-1-phenyl-2-[(S)-1-azidopropyl]-N,N-di-isobutylcyclopropanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-1-phenyl-2-[(S)-1-azidopropyl]-N,N-di-isobutylcyclopropanecarboxamide

There total 5 articles about (1S,2R)-1-phenyl-2-[(S)-1-azidopropyl]-N,N-di-isobutylcyclopropanecarboxamide 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: 68.0%

(1S,2R)-1-phenyl-2-[(S)-1-hydroxypropyl]-N,N-di-isobutylcyclopropanecarboxamide (459143-48-7) → (1S,2R)-1-phenyl-2-[(S)-1-azidopropyl]-N,N-di-isobutylcyclopropanecarboxamide (459143-54-5)

Guidance literature:

(1S,2R)-1-phenyl-2-[(S)-1-hydroxypropyl]-N,N-di-isobutylcyclopropanecarboxamide; With carbon tetrabromide; triphenylphosphine; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 0 ℃; for 0.5h;

With sodium azide; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 20 ℃; for 6h;

DOI:10.1016/S0968-0896(02)00030-5

Reference yield:

diisobutylamine (110-96-3) → (1S,2R)-1-phenyl-2-[(S)-1-azidopropyl]-N,N-di-isobutylcyclopropanecarboxamide (459143-54-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 93 percent / AlCl₃ / CH₂Cl₂ / 24 h / 20 °C

2.1: 77 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

3.1: 82 percent / tetrahydrofuran; diethyl ether / 3 h / -15 °C

4.1: PPh₃CBr₄ / hexamethylphosphoric acid triamide / 0.5 h / 0 °C

4.2: 68 percent / NaN₃ / hexamethylphosphoric acid triamide / 6 h / 20 °C

With aluminium trichloride; oxalyl dichloride; carbon tetrabromide; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; 2.1: Swern oxidation / 3.1: Grignard reaction;

DOI:10.1016/S0968-0896(02)00030-5

Reference yield:

(1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one (63106-93-4,96847-52-8,96847-75-5,96847-53-9) → (1S,2R)-1-phenyl-2-[(S)-1-azidopropyl]-N,N-di-isobutylcyclopropanecarboxamide (459143-54-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 93 percent / AlCl₃ / CH₂Cl₂ / 24 h / 20 °C

2.1: 77 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

3.1: 82 percent / tetrahydrofuran; diethyl ether / 3 h / -15 °C

4.1: PPh₃CBr₄ / hexamethylphosphoric acid triamide / 0.5 h / 0 °C

4.2: 68 percent / NaN₃ / hexamethylphosphoric acid triamide / 6 h / 20 °C

With aluminium trichloride; oxalyl dichloride; carbon tetrabromide; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; 2.1: Swern oxidation / 3.1: Grignard reaction;

DOI:10.1016/S0968-0896(02)00030-5

upstream raw materials:

(1S,2R)-1-phenyl-2-[(S)-1-hydroxypropyl]-N,N-di-isobutylcyclopropanecarboxamide

diisobutylamine

(1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one

(1S,2R)-1-phenyl-2-formyl-N,N-di-isobutylcyclopropanecarboxamide