Tert-butyl 4-(2-oxoethyl)piperidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 4-(2-oxoethyl)piperidine-1-carboxylate
• CAS No.: 142374-19-4
• Molecular Formula: C12H21 N O3
• Molecular Weight: 227.304
• European Community (EC) Number: 626-367-2
• DSSTox Substance ID: DTXSID80438584
• Nikkaji Number: J2.669.882K
• Wikidata: Q72503919
• Mol file: 142374-19-4.mol

Synonyms:142374-19-4;Tert-butyl 4-(2-oxoethyl)piperidine-1-carboxylate;N-Boc-4-piperidineacetaldehyde;1-PIPERIDINECARBOXYLIC ACID, 4-(2-OXOETHYL)-, 1,1-DIMETHYLETHYL ESTER;4-(2-oxoethyl)piperidine-1-carboxylic acid,tert-butyl ester;tert-Butyl 4-(formylmethyl)piperidine-1-carboxylate;MFCD03425258;4-(2-Oxoethyl)piperidine-1-carboxylic Acid tert-Butyl Ester;1-(tert-Butoxycarbonyl)piperidine-4-acetaldehyde;4-(2-Oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester;tert-Butyl4-(2-oxoethyl)piperidine-1-carboxylate;SCHEMBL416508;N-Boc-4-piperidine acetaldehyde;DTXSID80438584;PSRHRFNKESVOEL-UHFFFAOYSA-N;CS-M1538;AKOS005067591;N-Boc-4-piperidineacetaldehyde, 97%;AB14633;N-BOC-PIPERIDINYL-4-ACETALDEHYDE;AM803210;DS-12138;SY014443;FT-0649356;N-tert-Butoxycarbonyl-4-piperidylacetaldehyde;(1-t-butoxycarbonylpiperidin4-yl)acetaldehyde;1-t-butyloxycarbonyl-4-formylmethyl-piperidine;EN300-66955;(1-t -Butoxycarbonylpiperidin4-yl)acetaldehyde;(1-t-Butoxycarbonylpiperidin-4-yl)acetaldehyde;A20260;1-tert-butoxycarbonyl-4-(formylmethyl)piperidine;tert-butyl 4-(oxoethyl)piperidine-1-carboxylate;1-(tert-butoxycarbonyl)-piperidine-4-acetaldehyde;tert-butyl-4-(2-oxoethyl)piperidine-1-carboxylate;[1-(tert-butoxycarbonyl)piperidin-4-yl]acetaldehyde;2-(N-t-Butyloxycarbonylpiperidin-4-yl)acetaldehyde;tert-butyl 4-(2-oxo-ethyl)piperidine-1-carboxylate;W-205578;[1-(tert-butoxycarbonyl)piperidin -4-yl]acetaldehyde;Z1065726098;1,1-dimethylethyl 4-(2-oxoethyl)-1-piperidinecarboxylate;4-(2-oxoethyl)piperidin 1-carboxylic acid tert-butyl ester;4-(2-OxoEthyl)piperidine-1-carboxylic acidtert-butyl ester;4-(2-oxo-ethyl)piperidine-1-carboxylic acid tert-butyl ester;1-Piperidinecarboxylic acid,4-(2-oxoethyl)-,1,1-dimethylethyl ester;4-(2-Oxoethyl)piperidine-1-carboxylic acid, tert-butyl ester, tert-Butyl 4-(formylmethyl)piperidine-1-carboxylate

Chemical Property of Tert-butyl 4-(2-oxoethyl)piperidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 38-42 °C
• Refractive Index: 1.467
• Boiling Point: 318.1°Cat760mmHg
• PKA: -1.62±0.40(Predicted)
• Flash Point: 146.2°C
• PSA: 46.61000
• Density: 1.035g/cm³
• LogP: 2.16040
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 227.15214353
• Heavy Atom Count: 16
• Complexity: 250

Purity/Quality:

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

N-Boc-4-piperidineacetaldehyde ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(CC1)CC=O
• Uses: N-Boc-4-piperidineacetaldehyde is used in the preparation of benzofuran-2-carboxylic acid based Pim-1 inhibitors. Reactant for synthesis of:Pim-1 inhibitorsSelective GPR119 agonists for type II diabetesReactant for: α-arylation of aldehydesEnantioselective α-benzylation of aldehydes via photoredox organocatalysisEnantioselective α?triflouromethylation of aldehydes

Technology Process of Tert-butyl 4-(2-oxoethyl)piperidine-1-carboxylate

There total 18 articles about Tert-butyl 4-(2-oxoethyl)piperidine-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-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester (89151-44-0) → tert-butyl 4-(formylmethyl)piperidine-1-carboxylate (142374-19-4)

Guidance literature:

With oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; at -60 ℃; for 1.5h;

Reference yield: 93.0%

tert-butyl 4-(2-oxoethylidene)piperidine-1-carboxylate (502609-58-7) → tert-butyl 4-(formylmethyl)piperidine-1-carboxylate (142374-19-4)

Guidance literature:

With triethylsilane; palladium dichloride; tricyclohexylphosphine; In tetrahydrofuran; water; at 20 ℃; for 1h;

DOI:10.1002/chem.201100655

Reference yield: 67.0%

tert-butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate (135716-09-5) → tert-butyl 4-(formylmethyl)piperidine-1-carboxylate (142374-19-4)

Guidance literature:

With diisobutylaluminium hydride; In hexane; toluene; at -78 ℃; for 0.166667h;

DOI:10.3987/com-00-8965

upstream raw materials:

4-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester

tert-butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate

4-(2-Hydroxyethyl)piperidine

di-tert-butyl dicarbonate

Downstream raw materials:

N-<<3(R)-(-)-<2-(piperidin-4-yl)ethyl>-2-oxopiperidin-1-yl>acetyl>-3(R)-methyl-β-alanine

(S)-tert-butyl 4-(1-(2,4-dinitrophenyl)-3-oxopropan-2-yl)piperidine-1-carboxylate

Refernces

• 1、 Saito, Masato,Kawamata, Yu,Meanwell, Michael,Navratil, Rafael,Chiodi, Debora,Carlson, Ethan,Hu, Pengfei,Chen, Longrui,Udyavara, Sagar,Kingston, Cian,Tanwar, Mayank,Tyagi, Sameer,McKillican, Bruce P.,Gichinga, Moses G.,Schmidt, Michael A.,Eastgate, Martin D.,Lamberto, Massimiliano,He, Chi,Tang, Tianhua,Malapit, Christian A.,Sigman, Matthew S.,Minteer, Shelley D.,Neurock, Matthew,Baran, Phil S.. "N-Ammonium Ylide Mediators for Electrochemical C-H Oxidation". supporting information. p. 7859 - 7867. Retrieved 2021/05/26.
• 2、 Lakeland, Christopher P.,Watson, David W.,Harrity, Joseph P. A.. "Exploiting Synergistic Catalysis for an Ambient Temperature Photocycloaddition to Pyrazoles". supporting information. p. 155 - 159. Retrieved 2019/12/11.