Tert-butyl 4-ethynyl-4-hydroxypiperidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 4-ethynyl-4-hydroxypiperidine-1-carboxylate
• CAS No.: 275387-83-2
• Molecular Formula: C12H19NO3
• Molecular Weight: 225.288
• European Community (EC) Number: 823-037-1
• Mol file: 275387-83-2.mol

Synonyms:275387-83-2;tert-butyl 4-ethynyl-4-hydroxypiperidine-1-carboxylate;1-Boc-4-ethynyl-4-hydroxypiperidine;4-Ethynyl-1-tert-butoxycarbonylpiperidin-4-ol;N-Boc-4-hydroxy-4-ethynyl-piperidine;1-Piperidinecarboxylic acid, 4-ethynyl-4-hydroxy-, 1,1-dimethylethyl ester;MFCD20483708;SCHEMBL2110226;1-Boc-4-ethynylpiperidin-4-ol;tert-Butyl 4-ethynyl-4-hydroxy-piperidine-1-carboxylate;SHEYWYIIXFHSNB-UHFFFAOYSA-N;4-ethynyl-4-hydroxypiperidine-1-carboxylic acid tert-butyl ester;AMY35537;CS-D1232;AKOS025290026;PB36213;SB20699;AS-51480;SY116191;DB-320999;tert-butyl 4-ethynyl-4-hydroxypiperidine-1-;EN300-313930;P12768;A876902;tert-butyl4-ethynyl-4-hydroxypiperidine-1-carboxylate;F2147-8498;1,1-dimethylethyl 4-ethynyl-4-hydroxy-1-piperidinecarboxylate;4-Ethynyl-4-Hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property of Tert-butyl 4-ethynyl-4-hydroxypiperidine-1-carboxylate

Chemical Property:

• Boiling Point: 310.9±42.0 °C(Predicted)
• PKA: 12.84±0.20(Predicted)
• PSA: 49.77000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 1.31950
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 225.13649347
• Heavy Atom Count: 16
• Complexity: 313

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Boc-4-ethynyl-4-hydroxypiperidine ^*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)(C#C)O
• Uses: 1-Boc-4-ethynyl-4-hydroxypiperidine is used in preparation of heteroaryl-substituted pyrazolo[1,5-a]pyridines as RET inhibitors, pharmaceutical compounds and uses thereof.

Technology Process of Tert-butyl 4-ethynyl-4-hydroxypiperidine-1-carboxylate

There total 8 articles about Tert-butyl 4-ethynyl-4-hydroxypiperidine-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: 100.0%

4-hydroxy-4-trimethylsilanylethynylpiperidine-1-carboxylic acid tert-butyl ester (185132-51-8) → 4-ethynyl-4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (275387-83-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 25 ℃; for 12h;

Reference yield: 92.0%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + trimethylsilylacetylene (1066-54-2) → 4-ethynyl-4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (275387-83-2)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -75 ℃; for 1h; Inert atmosphere;

N-tert-butyloxycarbonylpiperidin-4-one; In tetrahydrofuran; hexane; at -75 - 20 ℃; for 4.16667h; Inert atmosphere;

With potassium carbonate; In tetrahydrofuran; methanol; hexane; at 20 ℃; for 5h;

Reference yield: 82.0%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + acetylenemagnesium bromide (4301-14-8) → 4-ethynyl-4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (275387-83-2)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1002/anie.201506882

upstream raw materials:

4-hydroxy-4-trimethylsilanylethynylpiperidine-1-carboxylic acid tert-butyl ester

ethynylmagnesium chloride

N-tert-butyloxycarbonylpiperidin-4-one

acetylenemagnesium bromide

Downstream raw materials:

1,1-dimethylethyl 4-hydroxy-4-{[6-(methyloxy)-1,5-naphthyridin-4-yl]ethynyl}-1-piperidinecarboxylate

tert-butyl 4-[2-(3-cyano-4-fluorophenyl)ethyl]-4-hydroxypiperidine-1-carboxylate

tert-butyl 4-[(3-cyano-4-fluorophenyl)ethynyl]-4-hydroxypiperidine-1-carboxylate

tert-butyl 4-hydroxy-4-{1-[(4-methylphenyl)sulfonyl]-1H-1,2,3-triazol-4-yl}piperidine-1-carboxylate

Refernces

• 1、 -. "Novel RET inhibitors. Pharmaceutical composition and use thereof". Paragraph 0331-0334. . Retrieved 2021/11/10.
• 2、 -. "6,7,8,9-TETRAHYDRO-5H-PYRIDO[2,3-d]AZEPINE DOPAMINE D3 LIGANDS". Page/Page column 69. . Retrieved 2017/08/30.