Tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate
• CAS No.: 158144-85-5
• Molecular Formula: C17H25NO3
• Molecular Weight: 291.39
• DSSTox Substance ID: DTXSID50433900
• Nikkaji Number: J1.323.818I
• Wikidata: Q82248173
• Mol file: 158144-85-5.mol

Synonyms:TERT-BUTYL 4-(HYDROXYMETHYL)-4-PHENYLPIPERIDINE-1-CARBOXYLATE;158144-85-5;SCHEMBL2270783;DTXSID50433900;Tert-butyl 4-(hydroxymethyl)-4-phenyl-piperidine-1-carboxylate;MFCD11044987;AKOS007930857;SB15560;AS-41634;CS-0054406;FT-0729058;EN300-4353972;A883450;1-tert-Butoxycarbonyl-4-phenyl-4-hydroxymethyl piperidine;tert-butyl4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate;(+/-)-tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate;4-(hydroxymethyl)-4-phenyl-1-piperidinecarboxylic acid tert-butyl ester;4-Phenyl-4-(hydroxymethyl)piperidine-1-carboxylic acid tert-butyl ester

Chemical Property of Tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate

Chemical Property:

• Boiling Point: 410.7±38.0 °C(Predicted)
• PKA: 14.94±0.10(Predicted)
• PSA: 49.77000
• Density: 1.095±0.06 g/cm3(Predicted)
• LogP: 2.88550
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 291.18344366
• Heavy Atom Count: 21
• Complexity: 348

Purity/Quality:

NLT 98% ^*data from raw suppliers

tert-Butyl4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(CC1)(CO)C2=CC=CC=C2

Technology Process of Tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate

There total 10 articles about Tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate 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: 97.0%

N-(t-butyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid (167262-68-2) → 1-t-butoxycarbonyl-4-phenyl-4-hydroxymethyl piperidine (158144-85-5)

Guidance literature:

N-(t-butyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid; With borane-THF; In tetrahydrofuran; at 20 ℃; for 72h;

With sodium hydroxide; In tetrahydrofuran; at 0 ℃;

Reference yield: 69.0%

di-tert-butyl dicarbonate (24424-99-5) + 4-phenyl-4-piperidinecarboxylic acid 4-methylbenzenesulfonate → 1-t-butoxycarbonyl-4-phenyl-4-hydroxymethyl piperidine (158144-85-5)

Guidance literature:

4-phenyl-4-piperidinecarboxylic acid 4-methylbenzenesulfonate; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1.5h; Heating / reflux;

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

di-tert-butyl dicarbonate; In tetrahydrofuran; dichloromethane; water; at 20 ℃; for 18h;

Reference yield: 63.0%

tert-butyldicarbonate (34619-03-9) + 4-phenyl-4-piperidinecarboxylic acid 4-methylbenzenesulfonate → 1-t-butoxycarbonyl-4-phenyl-4-hydroxymethyl piperidine (158144-85-5)

Guidance literature:

4-phenyl-4-piperidinecarboxylic acid 4-methylbenzenesulfonate; With borane-THF; In tetrahydrofuran; at 0 - 20 ℃;

tert-butyldicarbonate; With sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; Product distribution / selectivity;

upstream raw materials:

4-phenyl-piperidine-4-carboxylic acid

di-tert-butyl dicarbonate

(4-phenyl-piperidin-4-yl)-methanol

N-(t-butyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid

Downstream raw materials:

C₂₃H₂₈Cl₂N₂O₃

C₂₄H₃₃N₃O₅

tert-butyl 4-(((6-chloro-4-(trifluoromethyl)pyridine-2-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate

tert-butyl 4-(((5-bromopyridin-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate

Refernces

• 1、 -. "Substituted Heterocyclic Ethers and Their Use in CNS Disorders". Page/Page column 41. . Retrieved 2009/01/24.
• 2、 -. "SUBSTITUTED HETEROCYCLIC ETHERS AND THEIR USE IN CNS DISORDERS". Page/Page column 29. . Retrieved 2008/06/13.