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

Base Information

• Chemical Name: (1S,2R)-{N-benzyl-N-[(1R)-1-phenylethyl]}-2-vinylcyclopropanamine
• CAS No.: 1338807-46-7
• Molecular Formula: C₂₀H₂₃N
• Molecular Weight: 277.409
• Mol file: 1338807-46-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (1S,2R)-{N-benzyl-N-[(1R)-1-phenylethyl]}-2-vinylcyclopropanamine 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: 36.0%

(R)-N-benzyl-N-(α-methylbenzyl)formamide (1338807-53-6) + 4-but-1-enylmagnesium bromide (7103-09-5) → (1R,2S)-{N-benzyl-N-[(1R)-1-phenylethyl]}-2-vinylcyclopropanamine (1338807-45-6) + (1S,2R)-{N-benzyl-N-[(1R)-1-phenylethyl]}-2-vinylcyclopropanamine (1338807-46-7) + (Z)-{N-benzyl-N-[(1R)-1-phenylethyl]}-2-vinylcyclopropanamine (1338807-47-8)

Guidance literature:

With methyltriisopropoxytitanium(IV); In tetrahydrofuran; at 0 - 20 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1039/c1ob06095c

Reference yield:

(R)-N-benzyl-1-phenylethylamine (38235-77-7) → (1S,2R)-{N-benzyl-N-[(1R)-1-phenylethyl]}-2-vinylcyclopropanamine (1338807-46-7)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 1 h / 20 °C / Inert atmosphere

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

With methyltriisopropoxytitanium(IV); In tetrahydrofuran; dichloromethane; 2: Kulinkovich de Meijere reaction;

DOI:10.1039/c1ob06095c

Reference yield: 96.0%

(1S,2R)-{N-benzyl-N-[(1R)-1-phenylethyl]}-2-vinylcyclopropanamine (1338807-46-7) → 2-{(1R,2S)-2-(N-benzyl-N-[(1R)-1-phenylethyl]amino)cyclopropyl}ethanol (1338807-49-0)

Guidance literature:

(1S,2R)-{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

upstream raw materials:

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

4-but-1-enylmagnesium bromide

(R)-N-benzyl-1-phenylethylamine

Downstream raw materials:

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

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

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

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