2-{(1S,2R)-2-(N-benzyl-N-[(1R)-1-phenylethyl]amino)cyclopropyl}ethanol

Base Information

• Chemical Name: 2-{(1S,2R)-2-(N-benzyl-N-[(1R)-1-phenylethyl]amino)cyclopropyl}ethanol
• CAS No.: 1338807-48-9
• Molecular Formula: C₂₀H₂₅NO
• Molecular Weight: 295.425
• Mol file: 1338807-48-9.mol

Synonyms:2-{(1S,2R)-2-(N-benzyl-N-[(1R)-1-phenylethyl]amino)cyclopropyl}ethanol

Chemical Property of 2-{(1S,2R)-2-(N-benzyl-N-[(1R)-1-phenylethyl]amino)cyclopropyl}ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(1S,2R)-2-(N-benzyl-N-[(1R)-1-phenylethyl]amino)cyclopropyl}ethanol

There total 6 articles about 2-{(1S,2R)-2-(N-benzyl-N-[(1R)-1-phenylethyl]amino)cyclopropyl}ethanol 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: 95.0%

(1R,2S)-{N-benzyl-N-[(1R)-1-phenylethyl]}-2-vinylcyclopropanamine (1338807-45-6) → 2-{(1S,2R)-2-(N-benzyl-N-[(1R)-1-phenylethyl]amino)cyclopropyl}ethanol (1338807-48-9)

Guidance literature:

(1R,2S)-{N-benzyl-N-[(1R)-1-phenylethyl]}-2-vinylcyclopropanamine; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c1ob06095c

Reference yield: 74.0%

(1R,2S)-{N-benzyl-N-[(1R)-1-phenylethyl]}-2-vinylcyclopropanamine (1338807-45-6) → (1R,2R)-{N-benzyl-N-[(1R)-1-phenylethyl]}-2-ethylcyclopropanamine (1338807-51-4) + 2-{(1S,2R)-2-(N-benzyl-N-[(1R)-1-phenylethyl]amino)cyclopropyl}ethanol (1338807-48-9)

Guidance literature:

(1R,2S)-{N-benzyl-N-[(1R)-1-phenylethyl]}-2-vinylcyclopropanamine; With borane-THF; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c1ob06095c

Reference yield:

(R)-N-benzyl-N-(α-methylbenzyl)formamide (1338807-53-6) → 2-{(1S,2R)-2-(N-benzyl-N-[(1R)-1-phenylethyl]amino)cyclopropyl}ethanol (1338807-48-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methyltriisopropoxytitanium(IV) / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

With methyltriisopropoxytitanium(IV); 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; 1.1: Kulinkovich de Meijere reaction;

DOI:10.1039/c1ob06095c

upstream raw materials:

(R)-N-benzyl-N-(α-methylbenzyl)formamide

(1R,2S)-{N-benzyl-N-[(1R)-1-phenylethyl]}-2-vinylcyclopropanamine

(R)-N-benzyl-1-phenylethylamine

Downstream raw materials:

tert-butyl [(1R,2S)-2-(2-hydroxyethyl)cyclopropyl][(1R)-1-phenylethyl]carbamate

tert-butyl [(1R,2S)-2-(2-hydroxyethyl)cyclopropyl]carbamate

(1S,2R)-2-(t-buthoxycarbonyl)amino-1-(carboxymethyl)cyclopropane