(1S,2R)-1-phenyl-2-(hydroxymethyl)-N,N-dibutylcyclopropanecarboxamide

Base Information

• Chemical Name: (1S,2R)-1-phenyl-2-(hydroxymethyl)-N,N-dibutylcyclopropanecarboxamide
• CAS No.: 459143-32-9
• Molecular Formula: C₁₉H₂₉NO₂
• Molecular Weight: 303.445
• Mol file: 459143-32-9.mol

Synonyms:(1S,2R)-1-phenyl-2-(hydroxymethyl)-N,N-dibutylcyclopropanecarboxamide

Chemical Property of (1S,2R)-1-phenyl-2-(hydroxymethyl)-N,N-dibutylcyclopropanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-1-phenyl-2-(hydroxymethyl)-N,N-dibutylcyclopropanecarboxamide

There total 1 articles about (1S,2R)-1-phenyl-2-(hydroxymethyl)-N,N-dibutylcyclopropanecarboxamide 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: 94.0%

(1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one (63106-93-4,96847-52-8,96847-75-5,96847-53-9) + dibutylamine (111-92-2) → (1S,2R)-1-phenyl-2-(hydroxymethyl)-N,N-dibutylcyclopropanecarboxamide (459143-32-9)

Guidance literature:

With aluminium trichloride; In dichloromethane; at 20 ℃; for 24h;

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

Reference yield: 96.0%

(1S,2R)-1-phenyl-2-(hydroxymethyl)-N,N-dibutylcyclopropanecarboxamide (459143-32-9) → (1S,2R)-1-phenyl-2-formyl-N,N-dibutylcyclopropanecarboxamide (459143-39-6)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;

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

Reference yield:

(1S,2R)-1-phenyl-2-(hydroxymethyl)-N,N-dibutylcyclopropanecarboxamide (459143-32-9) → (1S,2R)-1-phenyl-2-[(S)-1-aminopropyl]-N,N-dibutylcyclopropanecarboxamide hydrochloride

Guidance literature:

Multi-step reaction with 4 steps

1.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

2.1: 69 percent / tetrahydrofuran; diethyl ether / 3 h / -15 °C

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

3.2: 62 percent / NaN₃ / hexamethylphosphoric acid triamide / 6 h / 20 °C

4.1: 96 percent / H₂ / 10 percent Pd/C / methanol / 18 h / 20 °C / atmospheric pressure

With oxalyl dichloride; carbon tetrabromide; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; 1.1: Swern oxidation / 2.1: Grignard reaction;

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

upstream raw materials:

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

dibutylamine

Downstream raw materials:

(1S,2R)-1-phenyl-2-formyl-N,N-dibutylcyclopropanecarboxamide

(1S,4S,5R)-2-oxo-4-ethyl-1-phenyl-3-oxabicyclo[3.1.0]hexane

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

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