1-BOC-4-(4-METHOXYPHENYL)-4-HYDROXYPIPERIDINE

Base Information

• Chemical Name: 1-BOC-4-(4-METHOXYPHENYL)-4-HYDROXYPIPERIDINE
• CAS No.: 302924-67-0
• Molecular Formula: C₁₇H₂₅NO₄
• Molecular Weight: 307.39
• Mol file: 302924-67-0.mol

Synonyms:tert-butyl 4-hydroxy-4-(4-methoxyphenyl)-1-piperidinecarboxylate

Chemical Property of 1-BOC-4-(4-METHOXYPHENYL)-4-HYDROXYPIPERIDINE

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

1-Boc-4-(4-methoxyphenyl)-4-hydroxypiperidine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-BOC-4-(4-METHOXYPHENYL)-4-HYDROXYPIPERIDINE

There total 5 articles about 1-BOC-4-(4-METHOXYPHENYL)-4-HYDROXYPIPERIDINE 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%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + 4-methoxyphenyl magnesium bromide (13139-86-1) → tert-butyl 4-hydroxy-4-(4-methoxyphenyl)-1-piperidinecarboxylate (302924-67-0)

Guidance literature:

In diethyl ether; at 0 - 20 ℃; for 2h;

Reference yield: 97.0%

t-butyl 4-hydroxy piperidine-1-carboxylate (109384-19-2) + 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane (213596-33-9) → tert-butyl 4-hydroxy-4-(4-methoxyphenyl)-1-piperidinecarboxylate (302924-67-0)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; potassium tert-butylate; chlorobenzene; cesium fluoride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; In toluene; at 80 ℃; for 0.5h; Inert atmosphere;

DOI:10.1039/c1cc10826c

Reference yield: 96.0%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane (213596-33-9) → tert-butyl 4-hydroxy-4-(4-methoxyphenyl)-1-piperidinecarboxylate (302924-67-0)

Guidance literature:

With C₆₂H₇₄Cl₂N₄Pd₂S₂; potassium carbonate; In toluene; at 120 ℃; for 18h; Inert atmosphere; Sealed tube;

DOI:10.1002/cctc.202001464

upstream raw materials:

1-bromo-4-methoxy-benzene

N-tert-butyloxycarbonylpiperidin-4-one

4-methoxyphenyl magnesium bromide

4-methoxyphenylboronic acid

Downstream raw materials:

4-(4-methoxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

4-(4-methoxylphenyl)pyridine

4-(4-methoxy-phenyl)-3,6-dihydro-2H-pyridine-1-sulfonyl chloride

4-(4-methoxyphenyl)-1,2,3,6-tetrahydro-pyridine

Refernces

• 1、 Croft, Rosemary A.,Dubois, Maryne A. J.,Boddy, Alexander J.,Denis, Camille,Lazaridou, Anna,Voisin-Chiret, Anne Sophie,Bureau, Ronan,Choi, Chulho,Mousseau, James J.,Bull, James A.. "Catalytic Friedel-Crafts Reactions on Saturated Heterocycles and Small Rings for sp3-sp2 Coupling of Medicinally Relevant Fragments". supporting information. p. 5385 - 5395. Retrieved 2019/06/24.
• 2、 Toscani, Anita,Risi, Caterina,Black, Gary W.,Brown, Nicola L.,Shaaban, Ali,Turner, Nicholas J.,Castagnolo, Daniele. "Monoamine Oxidase (MAO-N) Whole Cell Biocatalyzed Aromatization of 1,2,5,6-Tetrahydropyridines into Pyridines". . p. 8781 - 8787. Retrieved 2018/09/06.