2-amino-2-((benzylamino)methyl)-6-boronohexanoic acid

Base Information

• Chemical Name: 2-amino-2-((benzylamino)methyl)-6-boronohexanoic acid
• CAS No.: 1345808-93-6
• Molecular Formula: C₁₄H₂₃BN₂O₄
• Molecular Weight: 294.159
• Mol file: 1345808-93-6.mol

Synonyms:

Chemical Property of 2-amino-2-((benzylamino)methyl)-6-boronohexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-amino-2-((benzylamino)methyl)-6-boronohexanoic acid

There total 9 articles about 2-amino-2-((benzylamino)methyl)-6-boronohexanoic acid 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:

diethyl 2-but-3-enyl-2-(tert-butoxycarbonylamino)propanedioate → 2-amino-2-((benzylamino)methyl)-6-boronohexanoic acid (1345808-93-6)

Guidance literature:

Multi-step reaction with 9 steps

1: potassium hydroxide / ethanol / 19 h / 0 - 20 °C

2: triethylamine

3: sodium tetrahydroborate / 1 h / -40 °C

4: dmap / dichloromethane / 16 h / 20 °C

5: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,2-bis-(diphenylphosphino)ethane / dichloromethane / 10 h / 20 °C

6: potassium carbonate / ethanol / 2 h / 20 °C

7: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

8: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 2 h / 60 °C

9: hydrogenchloride / 16 h / 95 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; oxalyl dichloride; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; 1,2-bis-(diphenylphosphino)ethane; potassium hydroxide; In ethanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/j.bmcl.2013.02.024

Reference yield:

2-(tert-butoxycarbonylamino)-2-(ethoxycarbonyl)hex-5-enoic acid (1345673-05-3) → 2-amino-2-((benzylamino)methyl)-6-boronohexanoic acid (1345808-93-6)

Guidance literature:

Multi-step reaction with 8 steps

1: triethylamine

2: sodium tetrahydroborate / 1 h / -40 °C

3: dmap / dichloromethane / 16 h / 20 °C

4: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,2-bis-(diphenylphosphino)ethane / dichloromethane / 10 h / 20 °C

5: potassium carbonate / ethanol / 2 h / 20 °C

6: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

7: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 2 h / 60 °C

8: hydrogenchloride / 16 h / 95 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; oxalyl dichloride; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; 1,2-bis-(diphenylphosphino)ethane; In ethanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/j.bmcl.2013.02.024

Reference yield:

ethyl 2-(tert-butoxycarbonylamino)-2-(hydroxymethyl)hex-5-enoate (1345673-06-4) → 2-amino-2-((benzylamino)methyl)-6-boronohexanoic acid (1345808-93-6)

Guidance literature:

Multi-step reaction with 6 steps

1: dmap / dichloromethane / 16 h / 20 °C

2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,2-bis-(diphenylphosphino)ethane / dichloromethane / 10 h / 20 °C

3: potassium carbonate / ethanol / 2 h / 20 °C

4: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

5: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 2 h / 60 °C

6: hydrogenchloride / 16 h / 95 °C

With hydrogenchloride; dmap; bis(1,5-cyclooctadiene)diiridium(I) dichloride; oxalyl dichloride; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; 1,2-bis-(diphenylphosphino)ethane; In ethanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/j.bmcl.2013.02.024

upstream raw materials:

2-(tert-butoxycarbonylamino)-2-(ethoxycarbonyl)hex-5-enoic acid

ethyl 2-(tert-butoxycarbonylamino)-2-(hydroxymethyl)hex-5-enoate

ethyl 2-(acetoxymethyl)-2-(tert-butoxycarbonylamino)hex-5-enoate

ethyl 2-(acetoxymethyl)-2-(tert-butoxycarbonylamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate