tert-butyl 3-{2-amino-6-[2-(benzyloxy)phenyl]-3-cyano-4-pyridinyl}-1-piperidinecarboxylate

Base Information

• Chemical Name: tert-butyl 3-{2-amino-6-[2-(benzyloxy)phenyl]-3-cyano-4-pyridinyl}-1-piperidinecarboxylate
• CAS No.: 406212-53-1
• Molecular Formula: C₂₉H₃₂N₄O₃
• Molecular Weight: 484.598
• Mol file: 406212-53-1.mol

Synonyms:tert-butyl 3-{2-amino-6-[2-(benzyloxy)phenyl]-3-cyano-4-pyridinyl}-1-piperidinecarboxylate

Chemical Property of tert-butyl 3-{2-amino-6-[2-(benzyloxy)phenyl]-3-cyano-4-pyridinyl}-1-piperidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 3-{2-amino-6-[2-(benzyloxy)phenyl]-3-cyano-4-pyridinyl}-1-piperidinecarboxylate

There total 7 articles about tert-butyl 3-{2-amino-6-[2-(benzyloxy)phenyl]-3-cyano-4-pyridinyl}-1-piperidinecarboxylate 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: 37.0%

2'-benzyloxyacetophenone (31165-67-0) + malononitrile (109-77-3) + 3-formylpiperidine-1-carboxylic acid tert-butyl ester (118156-93-7) → tert-butyl 3-{2-amino-6-[2-(benzyloxy)phenyl]-3-cyano-4-pyridinyl}-1-piperidinecarboxylate (406212-53-1)

Guidance literature:

With ammonium acetate; In 1,4-dioxane; at 120 ℃;

DOI:10.1016/j.bmcl.2004.05.041

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 3-{2-amino-6-[2-(benzyloxy)phenyl]-3-cyano-4-pyridinyl}-1-piperidinecarboxylate (406212-53-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / aq. NaOH / dioxane / 12 h / 20 °C

2: 100 percent / PyBOP; Et₃N / CH₂Cl₂ / 12 h / 20 °C

3: LiAlH₄ / tetrahydrofuran / 0.5 h / -15 °C

4: 34 percent / NH₄OAc / toluene / 2 h / 150 °C

With sodium hydroxide; lithium aluminium tetrahydride; ammonium acetate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; toluene;

DOI:10.1016/j.bmcl.2004.05.040

Reference yield:

N-(tert-butyloxycarbonyl)nipecotic acid (71381-75-4,88495-54-9,84358-12-3) → tert-butyl 3-{2-amino-6-[2-(benzyloxy)phenyl]-3-cyano-4-pyridinyl}-1-piperidinecarboxylate (406212-53-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / PyBOP; Et₃N / CH₂Cl₂ / 12 h / 20 °C

2: LiAlH₄ / tetrahydrofuran / 0.5 h / -15 °C

3: 34 percent / NH₄OAc / toluene / 2 h / 150 °C

With lithium aluminium tetrahydride; ammonium acetate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.bmcl.2004.05.040

upstream raw materials:

2'-benzyloxyacetophenone

malononitrile

3-formylpiperidine-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

6'-(2-benzyloxy-phenyl)-3'-cyano-2'-diacetylamino-3,4,5,6-tetrahydro-2H-[3,4']bipyridinyl-1-carboxylic acid tert-butyl ester

2'-amino-6'-(2-benzyloxy-phenyl)-1,2,3,4,5,6-hexahydro-[3,4']bipyridinyl-3'-carbonitrile

tert-butyl 3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-1-piperidinecarboxylate

tert-butyl 3-{2-bromo-6-[2-(benzyloxy)phenyl]-3-cyano-4-pyridinyl}-1-piperidinecarboxylate