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

Base Information

• Chemical Name: (1R,2S)-trans-2-(t-buthoxycarbonyl)amino-1-(carboxymethyl)cyclopropane
• CAS No.: 1338807-60-5
• Molecular Formula: C₁₀H₁₇NO₄
• Molecular Weight: 215.249
• Mol file: 1338807-60-5.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (1R,2S)-trans-2-(t-buthoxycarbonyl)amino-1-(carboxymethyl)cyclopropane 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: 55.0%

tert-butyl [(1S,2R)-2-(2-hydroxyethyl)cyclopropyl]carbamate (1338807-58-1,171550-09-7) → (1R,2S)-trans-2-(t-buthoxycarbonyl)amino-1-(carboxymethyl)cyclopropane (1338807-60-5,308266-57-1)

Guidance literature:

With potassium permanganate; sodium hydroxide; In water; tert-butyl alcohol; at 20 ℃; for 16h; Darkness; Inert atmosphere;

DOI:10.1039/c1ob06095c

Reference yield:

(1S,2R)-{N-benzyl-N-[(1R)-1-phenylethyl]}-2-vinylcyclopropanamine (1338807-46-7) → (1R,2S)-trans-2-(t-buthoxycarbonyl)amino-1-(carboxymethyl)cyclopropane (1338807-60-5,308266-57-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; formic acid / methanol / 4 h / Reflux; Inert atmosphere

2.2: 0 - 20 °C / pH 11 / Inert atmosphere

3.1: 20% palladium hydroxide on charcoal; hydrogen / tetrahydrofuran / 2 h / 20 °C / 760.05 Torr / Inert atmosphere

4.1: potassium permanganate; sodium hydroxide / water; tert-butyl alcohol / 16 h / 20 °C / Darkness; Inert atmosphere

With potassium permanganate; formic acid; palladium 10% on activated carbon; 20% palladium hydroxide on charcoal; hydrogen; 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide; In tetrahydrofuran; methanol; water; tert-butyl alcohol;

DOI:10.1039/c1ob06095c

Reference yield:

2-{(1R,2S)-2-(N-benzyl-N-[(1R)-1-phenylethyl]amino)cyclopropyl}ethanol (1338807-49-0) → (1R,2S)-trans-2-(t-buthoxycarbonyl)amino-1-(carboxymethyl)cyclopropane (1338807-60-5,308266-57-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium 10% on activated carbon; formic acid / methanol / 4 h / Reflux; Inert atmosphere

1.2: 0 - 20 °C / pH 11 / Inert atmosphere

2.1: 20% palladium hydroxide on charcoal; hydrogen / tetrahydrofuran / 2 h / 20 °C / 760.05 Torr / Inert atmosphere

3.1: potassium permanganate; sodium hydroxide / water; tert-butyl alcohol / 16 h / 20 °C / Darkness; Inert atmosphere

With potassium permanganate; formic acid; palladium 10% on activated carbon; 20% palladium hydroxide on charcoal; hydrogen; sodium hydroxide; In tetrahydrofuran; methanol; water; tert-butyl alcohol;

DOI:10.1039/c1ob06095c

upstream raw materials:

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

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