1-(benzyloxycarbonyl)-5-[1-(t-butoxycarbonyl)piperidin-4-yloxy]-2-(7-cyanonaphthalen-2-yl)indoline

Base Information

• Chemical Name: 1-(benzyloxycarbonyl)-5-[1-(t-butoxycarbonyl)piperidin-4-yloxy]-2-(7-cyanonaphthalen-2-yl)indoline
• CAS No.: 319451-92-8
• Molecular Formula: C₃₇H₃₇N₃O₅
• Molecular Weight: 603.718
• Mol file: 319451-92-8.mol

Synonyms:1-(benzyloxycarbonyl)-5-[1-(t-butoxycarbonyl)piperidin-4-yloxy]-2-(7-cyanonaphthalen-2-yl)indoline

Chemical Property of 1-(benzyloxycarbonyl)-5-[1-(t-butoxycarbonyl)piperidin-4-yloxy]-2-(7-cyanonaphthalen-2-yl)indoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(benzyloxycarbonyl)-5-[1-(t-butoxycarbonyl)piperidin-4-yloxy]-2-(7-cyanonaphthalen-2-yl)indoline

There total 6 articles about 1-(benzyloxycarbonyl)-5-[1-(t-butoxycarbonyl)piperidin-4-yloxy]-2-(7-cyanonaphthalen-2-yl)indoline 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: 100.0%

4-{4-benzyloxycarbonylamino-3-[2-(7-cyano-naphthalen-2-yl)-2-hydroxy-ethyl]-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester (319451-91-7) → 1-(benzyloxycarbonyl)-5-[1-(t-butoxycarbonyl)piperidin-4-yloxy]-2-(7-cyanonaphthalen-2-yl)indoline (319451-92-8)

Guidance literature:

With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; at 20 ℃;

DOI:10.1248/cpb.54.163

Reference yield:

tert-butyl 4-[4-nitro-3-(trimethylsilylmethyl)phenoxy]piperidine-1-carboxylate (319451-88-2) → 1-(benzyloxycarbonyl)-5-[1-(t-butoxycarbonyl)piperidin-4-yloxy]-2-(7-cyanonaphthalen-2-yl)indoline (319451-92-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: TBAF*H₂O / tetrahydrofuran / -10 °C

1.2: 64 percent / aq. TBAF / tetrahydrofuran / 20 °C

2.1: 86 percent / H₂ / Pd/C / ethanol; tetrahydrofuran / 20 °C

3.1: 93 percent / pyridine / N,N-dimethyl-acetamide; CH₂Cl₂ / 20 °C

4.1: 100 percent / n-Bu₃P; 1,1'-(azodicarbonyl)dipiperidine / tetrahydrofuran / 20 °C

With pyridine; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; 1,1'-azodicarbonyl-dipiperidine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide; 4.1: Mitsunobu reaction;

DOI:10.1248/cpb.54.163

Reference yield:

4-{3-[2-(7-cyano-naphthalen-2-yl)-2-hydroxy-ethyl]-4-nitro-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester (319451-89-3) → 1-(benzyloxycarbonyl)-5-[1-(t-butoxycarbonyl)piperidin-4-yloxy]-2-(7-cyanonaphthalen-2-yl)indoline (319451-92-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / H₂ / Pd/C / ethanol; tetrahydrofuran / 20 °C

2: 93 percent / pyridine / N,N-dimethyl-acetamide; CH₂Cl₂ / 20 °C

3: 100 percent / n-Bu₃P; 1,1'-(azodicarbonyl)dipiperidine / tetrahydrofuran / 20 °C

With pyridine; tributylphosphine; hydrogen; 1,1'-azodicarbonyl-dipiperidine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide; 3: Mitsunobu reaction;

DOI:10.1248/cpb.54.163

upstream raw materials:

4-{4-benzyloxycarbonylamino-3-[2-(7-cyano-naphthalen-2-yl)-2-hydroxy-ethyl]-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester

tert-butyl 4-[4-nitro-3-(trimethylsilylmethyl)phenoxy]piperidine-1-carboxylate

4-{3-[2-(7-cyano-naphthalen-2-yl)-2-hydroxy-ethyl]-4-nitro-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester

4-Fluoronitrobenzene