1-Piperidinecarboxylic acid, 3-hydroxy-4-[4-(phenylmethoxy)phenyl]-, 1,1-dimethylethyl ester, trans-

Base Information

• Chemical Name: 1-Piperidinecarboxylic acid, 3-hydroxy-4-[4-(phenylmethoxy)phenyl]-, 1,1-dimethylethyl ester, trans-
• CAS No.: 188867-89-2
• Molecular Formula: C₂₃H₂₉NO₄
• Molecular Weight: 383.488
• Mol file: 188867-89-2.mol

Synonyms:1-Piperidinecarboxylicacid, 3-hydroxy-4-[4-(phenylmethoxy)phenyl]-, 1,1-dimethylethyl ester, trans-

Chemical Property of 1-Piperidinecarboxylic acid, 3-hydroxy-4-[4-(phenylmethoxy)phenyl]-, 1,1-dimethylethyl ester, trans-

Chemical Property:

• PSA: 59.00000
• LogP: 4.28880

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Piperidinecarboxylic acid, 3-hydroxy-4-[4-(phenylmethoxy)phenyl]-, 1,1-dimethylethyl ester, trans-

There total 28 articles about 1-Piperidinecarboxylic acid, 3-hydroxy-4-[4-(phenylmethoxy)phenyl]-, 1,1-dimethylethyl ester, trans- 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: 95.0%

tert-butyl 4-(4-(benzyloxy)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-butyl (±)-(3RS,4RS)-4-(4-(benzyloxy)phenyl)-3-hydroxypiperidine-1-carboxylate (188867-89-2)

Guidance literature:

tert-butyl 4-(4-(benzyloxy)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate; With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at 20 ℃; for 2.25h; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; ethanol; water; at 70 ℃; Inert atmosphere;

DOI:10.1021/acs.oprd.8b00120

Reference yield:

tert-butyl 4-(4-(benzyloxy)phenyl)-3-(4-nitrobenzoyloxy)piperidine-1-carboxylate → tert-butyl 4-(4-(benzyloxy)phenyl)-3-hydroxypiperidine-1-carboxylate (188867-89-2)

Guidance literature:

With water; potassium hydroxide; In tetrahydrofuran; at 20 ℃;

Reference yield:

tert-butyl (±)-(3RS,4RS)-4-(4-(benzyloxy)phenyl)-3-hydroxypiperidine-1-carboxylate (188867-89-2) → (3S,4S)-tert-butyl 4-(4-(benzyloxy)phenyl)-3-hydroxypiperidine-1-carboxylate (188867-89-2)

Guidance literature:

With carbon dioxide; diethylamine; In methanol; Resolution of racemate;

upstream raw materials:

(3R,4R)-3-hydroxy-4-(4-hydroxy-phenyl)-piperidin-1-carboxylic-acid-tert-butylester

benzyl bromide

p-benzyloxyphenylbromide

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate

Refernces

• 1、 Kempson, James,Zhang, Huiping,Wong, Michael K. Y.,Li, Jianqing,Li, Peng,Wu, Dauh-Rurng,Rampulla, Richard,Galella, Michael A.,Dabros, Marta,Traeger, Sarah C.,Muthalagu, Vetrichelvan,Gupta, Anuradha,Arunachalam, Pirama Nayagam,Mathur, Arvind. "Evolution of a Scale-Up Synthesis to a Potent GluN2B Inhibitor and Its Prodrug". . p. 846 - 855. Retrieved 2018/06/13.
• 2、 -. "(R)-3-((3S,4S)-3-FLUORO-4-(4-HYDROXYPHENYL)PIPERIDIN-1-YL)-1-(4-METHYLBENZYL)PYRROLIDIN-2-ONE AND ITS PRODRUGS FOR THE TREATMENT OF PSYCHIATRIC DISORDERS". Paragraph 0028-0029. . Retrieved 2015/07/15.