2-Azabicyclo[2.2.2]octan-1-ylmethanol

Base Information

• Chemical Name: 2-Azabicyclo[2.2.2]octan-1-ylmethanol
• CAS No.: 936545-65-2
• Molecular Formula: C₈H₁₅NO
• Molecular Weight: 141.213
• European Community (EC) Number: 836-059-1
• DSSTox Substance ID: DTXSID001291802
• Nikkaji Number: J2.472.691F
• Mol file: 936545-65-2.mol

Synonyms:936545-65-2;2-Azabicyclo[2.2.2]octan-1-ylmethanol;2-Azabicyclo[2.2.2]octane-1-methanol;1-hydroxymethyl-2-azabicyclo[2,2,2]octane;{2-azabicyclo[2.2.2]octan-1-yl}methanol;DTXSID001291802;MFCD19686934;AKOS006380743;SB12612;s11236;PS-15465;SY283067;EN300-1168240

Chemical Property of 2-Azabicyclo[2.2.2]octan-1-ylmethanol

Chemical Property:

• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 141.115364102
• Heavy Atom Count: 10
• Complexity: 127

Purity/Quality:

≥98% ^*data from raw suppliers

2-Azabicyclo[2.2.2]octan-1-ylmethanol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC2(CCC1CN2)CO

Technology Process of 2-Azabicyclo[2.2.2]octan-1-ylmethanol

There total 6 articles about 2-Azabicyclo[2.2.2]octan-1-ylmethanol 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: 99.0%

2-benzyl-1-hydroxymethyl-2-azabicyclo[2.2.2]octane → 1-hydroxymethyl-2-azabicyclo[2.2.2]octane (936545-65-2)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; at 20 ℃; atmospheric pressure;

DOI:10.1021/jo0700732

Reference yield:

methyl 1-(benzamido)-4-methylenecyclohexanecarboxylate (936545-59-4) → 1-hydroxymethyl-2-azabicyclo[2.2.2]octane (936545-65-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / borane / tetrahydrofuran / 24 h / 0 °C

2: 99 percent / triethylamine / CH₂Cl₂ / 0 - 20 °C

3: 44 percent / potassium tert-butoxide / tetrahydrofuran / 18 h / 20 °C

4: 98 percent / LiAlH₄ / tetrahydrofuran / Heating

5: 99 percent / hydrogen / palladium(II) hydroxide on carbon / methanol / 20 °C / atmospheric pressure

With lithium aluminium tetrahydride; borane; potassium tert-butylate; hydrogen; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo0700732

Reference yield:

C16H21NO4 (936545-60-7) → 1-hydroxymethyl-2-azabicyclo[2.2.2]octane (936545-65-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / triethylamine / CH₂Cl₂ / 0 - 20 °C

2: 44 percent / potassium tert-butoxide / tetrahydrofuran / 18 h / 20 °C

3: 98 percent / LiAlH₄ / tetrahydrofuran / Heating

4: 99 percent / hydrogen / palladium(II) hydroxide on carbon / methanol / 20 °C / atmospheric pressure

With lithium aluminium tetrahydride; potassium tert-butylate; hydrogen; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo0700732

upstream raw materials:

methyl 1-(benzamido)-4-methylenecyclohexanecarboxylate

C₁₆H₂₁NO₄

C₁₇H₂₃NO₆S

methyl 1-benzimido-4-oxocyclohexane-1-carboxylate

Refernces