methyl (1S,2S,4R)-N-benzoyl-2-cyanomethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate

Base Information

• Chemical Name: methyl (1S,2S,4R)-N-benzoyl-2-cyanomethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate
• CAS No.: 869195-11-9
• Molecular Formula: C₁₇H₁₈N₂O₃
• Molecular Weight: 298.342
• Mol file: 869195-11-9.mol

Synonyms:methyl (1S,2S,4R)-N-benzoyl-2-cyanomethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate

Chemical Property of methyl (1S,2S,4R)-N-benzoyl-2-cyanomethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,2S,4R)-N-benzoyl-2-cyanomethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate

There total 5 articles about methyl (1S,2S,4R)-N-benzoyl-2-cyanomethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate 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: 76.0%

methyl (1S,2R,4R)-N-benzoyl-2-bromomethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate (869195-00-6) + potassium cyanide (151-50-8) → methyl (1S,2S,4R)-N-benzoyl-2-cyanomethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate (869195-11-9)

Guidance literature:

With 18-crown-6 ether; In N,N-dimethyl-formamide; at 80 ℃; for 24h;

DOI:10.1016/j.tetasy.2005.08.003

Reference yield:

methyl (1S,2R,4R)-N-benzoyl-2-methylsulfonyloxymethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate (869195-03-9) + potassium cyanide (151-50-8) → methyl (1S,2S,4R)-N-benzoyl-2-cyanomethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate (869195-11-9)

Guidance literature:

With 18-crown-6 ether; cesium fluoride; In N,N-dimethyl-formamide; at 90 ℃; for 24h;

DOI:10.1016/j.tetasy.2005.08.003

Reference yield:

methyl (1S,2R,4R)-N-benzoyl-2-formyl-7-azabicyclo[2.2.1]heptane-1-carboxylate (365538-26-7) → methyl (1S,2S,4R)-N-benzoyl-2-cyanomethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate (869195-11-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / sodium borohydride / methanol; H₂O / 0.83 h / 0 °C

2: 98 percent / triethylamine / CH₂Cl₂ / 0 - 20 °C

3: 75 percent / lithium bromide / dimethylformamide / 144 h / Heating

4: 76 percent / 18-crown-6 ether / dimethylformamide / 24 h / 80 °C

With sodium tetrahydroborate; 18-crown-6 ether; triethylamine; lithium bromide; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2005.08.003

upstream raw materials:

methyl (1S,2R,4R)-N-benzoyl-2-bromomethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate

potassium cyanide

methyl (1S,2R,4R)-N-benzoyl-2-methylsulfonyloxymethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate

methyl (1S,2R,4R)-N-benzoyl-2-formyl-7-azabicyclo[2.2.1]heptane-1-carboxylate