(R)-3-{3-[2-(4-Chloro-phenoxymethyl)-4-hydroxy-benzoimidazol-1-yl]-propyl}-piperidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (R)-3-{3-[2-(4-Chloro-phenoxymethyl)-4-hydroxy-benzoimidazol-1-yl]-propyl}-piperidine-1-carboxylic acid tert-butyl ester
• CAS No.: 210564-95-7
• Molecular Formula: C₂₇H₃₄ClN₃O₄
• Molecular Weight: 500.038
• Mol file: 210564-95-7.mol

Synonyms:(R)-3-{3-[2-(4-Chloro-phenoxymethyl)-4-hydroxy-benzoimidazol-1-yl]-propyl}-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property of (R)-3-{3-[2-(4-Chloro-phenoxymethyl)-4-hydroxy-benzoimidazol-1-yl]-propyl}-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-{3-[2-(4-Chloro-phenoxymethyl)-4-hydroxy-benzoimidazol-1-yl]-propyl}-piperidine-1-carboxylic acid tert-butyl ester

There total 10 articles about (R)-3-{3-[2-(4-Chloro-phenoxymethyl)-4-hydroxy-benzoimidazol-1-yl]-propyl}-piperidine-1-carboxylic acid tert-butyl ester 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: 74.0%

(R)-3-{3-[4-Benzyloxy-2-(4-chloro-phenoxymethyl)-benzoimidazol-1-yl]-propyl}-piperidine-1-carboxylic acid tert-butyl ester (193628-06-7) → (R)-3-{3-[2-(4-Chloro-phenoxymethyl)-4-hydroxy-benzoimidazol-1-yl]-propyl}-piperidine-1-carboxylic acid tert-butyl ester (210564-95-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 2h; under 760 Torr; Ambient temperature;

DOI:10.1021/jm9706630

Reference yield:

3-(piperidin-3-yl)propionic acid ethyl ester (91017-00-4) → (R)-3-{3-[2-(4-Chloro-phenoxymethyl)-4-hydroxy-benzoimidazol-1-yl]-propyl}-piperidine-1-carboxylic acid tert-butyl ester (210564-95-7)

Guidance literature:

Multi-step reaction with 6 steps

2: K₂CO₃ / tetrahydrofuran; H₂O / 6 h / Ambient temperature

3: LiAlH₄ / diethyl ether / 4 h / Ambient temperature

4: Ph₃P, Br₂, pyridine / CH₂Cl₂ / 6 h / Ambient temperature

5: 1.) NaH, 2.) KI / 1.) DMF, RT, 30 min, 2.) DMF, 80 deg C, 3 h

6: 74 percent / H₂ / 5percent Pd/C / ethyl acetate / 2 h / 760 Torr / Ambient temperature

With pyridine; lithium aluminium tetrahydride; hydrogen; bromine; sodium hydride; potassium carbonate; triphenylphosphine; potassium iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate;

DOI:10.1021/jm9706630

Reference yield:

(4-chlorophenoxy)acetonitrile (3598-13-8) → (R)-3-{3-[2-(4-Chloro-phenoxymethyl)-4-hydroxy-benzoimidazol-1-yl]-propyl}-piperidine-1-carboxylic acid tert-butyl ester (210564-95-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) MeONa / 1.) MeOH, RT, 30 min, 2.) MeOH, RT, 3 h

2: 53 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 6 h / Ambient temperature

3: 1.) NaH, 2.) KI / 1.) DMF, RT, 30 min, 2.) DMF, 80 deg C, 3 h

4: 74 percent / H₂ / 5percent Pd/C / ethyl acetate / 2 h / 760 Torr / Ambient temperature

With hydrogen; sodium methylate; sodium hydride; triphenylphosphine; potassium iodide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jm9706630

upstream raw materials:

(R)-3-{3-[4-Benzyloxy-2-(4-chloro-phenoxymethyl)-benzoimidazol-1-yl]-propyl}-piperidine-1-carboxylic acid tert-butyl ester

3-(piperidin-3-yl)propionic acid ethyl ester

(4-chlorophenoxy)acetonitrile

2-(4-Chloro-phenoxymethyl)-1H-benzoimidazol-4-ol

Downstream raw materials:

(R,R)-1-{3(R)-[N-(tert-butyloxycarbonyl)-3-piperidinyl]propyl}-2-[(4-chlorophenoxy)methyl]-4-({3(R)-[N-(tert-butyloxycarbonyl)-3-piperidinyl]propyl}oxy)benzimidazole

(R,S)-1-{3(R)-[N-(tert-butyloxycarbonyl)-3-piperidinyl]propyl}-2-[(4-chlorophenoxy)methyl]-4-({3(S)-[N-(tert-butyloxycarbonyl)-3-piperidinyl]propyl}oxy)benzimidazole