(1R,2S)-1-phenyl-2-methyl-2-(hydroxymethyl)-N,N-diethylcyclopropanecarboxamide

Base Information

• Chemical Name: (1R,2S)-1-phenyl-2-methyl-2-(hydroxymethyl)-N,N-diethylcyclopropanecarboxamide
• CAS No.: 345350-11-0
• Molecular Formula: C₁₆H₂₃NO₂
• Molecular Weight: 261.364
• Mol file: 345350-11-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (1R,2S)-1-phenyl-2-methyl-2-(hydroxymethyl)-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: 84.0%

lithium diethylamide (816-43-3) + (1R,5S)-5-methyl-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one (333956-68-6) → (1R,2S)-1-phenyl-2-methyl-2-(hydroxymethyl)-N,N-diethylcyclopropanecarboxamide (345350-11-0)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1002/1615-4169(20010330)343:3<299::AID-ADSC299>3.0.CO;2-Y

Reference yield:

2-methyl-2-propen-1-yl phenylacetate (128863-93-4) → (1R,2S)-1-phenyl-2-methyl-2-(hydroxymethyl)-N,N-diethylcyclopropanecarboxamide (345350-11-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene; p-acetylamino-benzenesulfonyl azide / acetonitrile / 20 °C

2: Rh₂[(4S)-4-methoxycarbonyl-1-azetin-2-olato-O,N]4 / CH₂Cl₂ / 4 h / 40 °C

3: 84 percent / tetrahydrofuran / 2 h / -78 °C

With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; Rh₂[(4S)-4-methoxycarbonyl-1-azetin-2-olato-O,N]4; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/1615-4169(20010330)343:3<299::AID-ADSC299>3.0.CO;2-Y

Reference yield:

phenylacetyl chloride (103-80-0) → (1R,2S)-1-phenyl-2-methyl-2-(hydroxymethyl)-N,N-diethylcyclopropanecarboxamide (345350-11-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / NEt₃ / CH₂Cl₂

2: 77 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene; p-acetylamino-benzenesulfonyl azide / acetonitrile / 20 °C

3: Rh₂[(4S)-4-methoxycarbonyl-1-azetin-2-olato-O,N]4 / CH₂Cl₂ / 4 h / 40 °C

4: 84 percent / tetrahydrofuran / 2 h / -78 °C

With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; Rh₂[(4S)-4-methoxycarbonyl-1-azetin-2-olato-O,N]4; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/1615-4169(20010330)343:3<299::AID-ADSC299>3.0.CO;2-Y

upstream raw materials:

lithium diethylamide

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

2-methyl-2-propen-1-yl phenylacetate

phenylacetyl chloride

Downstream raw materials:

(1R,2S)-1-phenyl-2-methyl-2-(azidomethyl)-N,N-diethylcyclopropanecarboxamide