Tert-butyl 4-formylpiperidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 4-formylpiperidine-1-carboxylate
• CAS No.: 137076-22-3
• Molecular Formula: C11H19NO3
• Molecular Weight: 213.277
• Hs Code.: 29333990
• European Community (EC) Number: 676-311-6
• DSSTox Substance ID: DTXSID60363885
• Nikkaji Number: J1.276.406E
• Wikidata: Q72450411
• Mol file: 137076-22-3.mol

Synonyms:137076-22-3;1-Boc-4-piperidinecarboxaldehyde;Tert-butyl 4-formylpiperidine-1-carboxylate;1-Boc-4-formylpiperidine;1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde;N-Boc-4-piperidinecarboxaldehyde;N-Boc-4-Formylpiperidine;4-Formylpiperidine-1-carboxylic acid tert-butyl ester;1-Boc-piperidine-4-carboxaldehyde;4-Formyl-Piperidine-1-Carboxylic Acid Tert-Butyl Ester;1-N-BOC-4-PIPERIDINECARBOXALDEHYDE;1-(tert-Butoxycarbonyl)-4-formylpiperidine;1-PIPERIDINECARBOXYLIC ACID, 4-FORMYL-, 1,1-DIMETHYLETHYL ESTER;MFCD02179019;tert-butyl 4-formyl-1-piperidinecarboxylate;1-(tert-Butoxycarbonyl)-4-piperidinecarboxaldehyde;1-(tert-butoxycarbonyl)piperidine-4-carbaldehyde;N-Boc-piperidine-4-carbaldehyde;N-Boc-4-formyl piperidine;N-Boc-4-piperidinemethanal;1-BOC-4-formyl-piperidine;SCHEMBL227336;DTXSID60363885;N-Boc piperidine-4-carboxaldehyde;1-Boc-4-piperidine-carboxaldehyde;1-N-BOC-4-FORMYLPIPERIDINE;BCP11759;CS-D0888;4-formyl-l-t-butoxycarbonylpiperidine;BBL101096;STL554890;1-t-Butoxycarbonyl-4-formylpiperidine;AKOS003637939;1-(t-butoxycarbonyl)4-formylpiperidine;1-t-butoxy carbonyl-4-formylpiperidine;AC-2841;PB23280;PS-3675;t-butyl 4-formylpiperidin-1-carboxylate;1-(t-Butoxycarbonyl)-4-formylpiperidine;1-tert-butoxycarbonyl-4-formylpiperidine;N-BOC-4-PIPERIDINYLCARBOXALDEHYDE;N-BOC-PIPERIDINE-4-CARBOXALDEHYDE;1-(t-butoxycarbonyl)-4-formyl piperidine;1-(t-Butoxycarbonyl)-4-formyl-piperidine;1-(tert-butoxycarbonyl)4-formylpiperidine;1-Boc-piperidine-4-carboxaldehyde, 95%;SY003093;t-butyl 4-formyl-piperidine-1-carboxylate;Tert-butyl4-formylpiperidine-1-carboxylate;1-(t-butoxycarbonyl)-piperidine-4-aldehyde;4-formyl-1-(tert-butoxycarbonyl)piperidine;tert-butyl-4-formyl-1-piperidinecarboxylate;tert-butyl-4-formylpiperidine-1-carboxylate;1-(tert-butyloxycarbonyl)-4-formylpiperidine;AM20080274;B3873;FT-0645168;tert-butyl 4-formylpiperidine-1 -carboxylate;tert-butyl-4-formyl-piperidine-1-carboxylate;1-(tert-butoxycarbonyl)-4-(formyl)piperidine;EN300-74115;1-(t-butoxycarbonyl)-4 piperidinecarboxaldehyde;1-(t-butoxycarbonyl)-4-piperidinecarboxaldehyde;1-tert-butoxycarbonyl-4-piperidine-carbaldehyde;N-tert-butoxycarbonyl-4-piperidinecarboxaldehyde;1-(t-butyloxycarbonyl)piperdine-4-carboxaldehyde;1-tert-butoxycarbonyl-piperidine-4-carboxaldehyde;1-(t-butyloxycarbonyl)piperidine-4-carboxaldehyde;1-(tert-butoxycarbonyl)piperidine-4-carboxaldehyde;4-Formyl-piperidine-carboxylic acid t-butyl ester;1-(1,1-Dimethylethyloxycarbonyl)-4-formylpiperidine;1-(tert-butoxycarbonyl)-piperidine-4-carboxaldehyde;4-Formyl-piperidine-1-carboxylic acid t-butyl ester;W-205495;4-Formylpiperidine-1-carboxilic acid tert-butyl ester;1-TERT-BUTOXYCARBONYLPIPERIDINE-4-CARBOXALDEHYDE;4-formyl-piperidine-1-carboxylic acid tert.-butyl ester;4-Formyl-piperidine-1-carboxylic acid, tert-butyl ester;Z1166113417;1,1-DIMETHYLETHYL 4-FORMYL-1-PIPERIDINECARBOXYLATE;4-formylpiperidine-1-carboxylic acid, 1,1-dimethylethyl ester;tert-butyl 4-formylpiperidine-1-carboxylate;N-BOC-PIPERIDINE-4-CARBALDEHYDE

Chemical Property of Tert-butyl 4-formylpiperidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 34-40℃
• Refractive Index: 1.519
• Boiling Point: 295.4 °C at 760 mmHg
• PKA: -2.13±0.40(Predicted)
• Flash Point: 132.5 °C
• PSA: 46.61000
• Density: 1.114 g/cm³
• LogP: 1.77030
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Sensitive.: Air Sensitive
• Solubility.: Soluble in methanol.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 213.13649347
• Heavy Atom Count: 15
• Complexity: 237

Purity/Quality:

98% ^*data from raw suppliers

4-Formylpiperidine-1-carboxylic Acid tert-Butyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N,Xn
• Statements: 36/37/38-50-22
• Safety Statements: 26-36/37/39-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(CC1)C=O
• Uses: Reactant for synthesis of:? ;Pim-1 inhibitors1? ;Selective GPR119 agonists for type II diabetes2? ;M-tropic (R5) HIV-1 replication inhibitors3? ;HDAC inhibitors4? ;Selective 5-HT6 antagonists5Reactant for three-component vinylogous Mannich reactions6 1-Boc-piperidine-4-carboxaldehyde is used as reactant for synthesis of Pim-1 inhibitors, selective GPR119 agonists for type II diabetes, M-tropic (R5) HIV-1 replication inhibitors, HDAC inhibitors and selective 5-HT6 antagonists. It is also used as reactant for three-component vinylogous Mannich reactions An intermediate for polycyclic indazole derivatives that are ERK inhibitors.

Technology Process of Tert-butyl 4-formylpiperidine-1-carboxylate

There total 30 articles about Tert-butyl 4-formylpiperidine-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%

tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (139290-70-3) → tert butyl 4-formylpiperidine-1-carboxylate (137076-22-3)

Guidance literature:

tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate; With lithium aluminium tetrahydride; In tetrahydrofuran; at -10 ℃; for 0.166667 - 0.333333h;

With hydrogenchloride; potassium hydrogensulfate; In tetrahydrofuran; water; for 0.25h;

Reference yield: 100.0%

tert-butyl 4-(hydroxymethyl)piperidin-1-carboxylate (123855-51-6) → tert butyl 4-formylpiperidine-1-carboxylate (137076-22-3)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1016/S0960-894X(00)00702-2

Reference yield: 95.0%

1-tert-Butyl 4-methyl piperidine-1,4-dicarboxylate (124443-68-1) → tert butyl 4-formylpiperidine-1-carboxylate (137076-22-3)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.5h;

upstream raw materials:

tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

tert-butyl 4-(hydroxymethyl)piperidin-1-carboxylate

1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

1-tert-Butyl 4-methyl piperidine-1,4-dicarboxylate

Downstream raw materials:

4-(3-benzyl-2-oxo-piperidin-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

C₁₉H₃₄N₂O₄

piperidine-4-carbaldehyde

4-(2,2-dibromo-vinyl)-piperidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Yamanaka, Toshio,Ohkubo, Mitsuru,Takahashi, Fumie,Kato, Masayuki. "An efficient synthesis of the orally-active GpIIb/IIIa antagonist FR184764". . p. 2843 - 2845. Retrieved 2004.
• 2、 Brindisi, Margherita,Senger, Johanna,Cavella, Caterina,Grillo, Alessandro,Chemi, Giulia,Gemma, Sandra,Cucinella, Dora Mariagrazia,Lamponi, Stefania,Sarno, Federica,Iside, Concetta,Nebbioso, Angela,Novellino, Ettore,Shaik, Tajith Baba,Romier, Christophe,Herp, Daniel,Jung, Manfred,Butini, Stefania,Campiani, Giuseppe,Altucci, Lucia,Brogi, Simone. "Novel spiroindoline HDAC inhibitors: Synthesis, molecular modelling and biological studies". . p. 127 - 138. Retrieved 2018.
• 3、 Hudak, Jason E.,Belardi, Brian,Appel, Mason J.,Solania, Angelo,Robinson, Peter V.,Bertozzi, Carolyn R.. "Piperidine-based glycodendrons as protein N-glycan prosthetics". . p. 4791 - 4800. Retrieved 2016.
• 4、 -. "BIFUNCTIONAL MOLECULES CONTAINING AN E3 UBIQUITINE LIGASE BINDING MOIETY LINKED TO A BCL6 TARGETING MOIETY". Paragraph 00475; 00476. . Retrieved 2021/04/23.
• 5、 Murugesan, Vetrivelan,Ganguly, Anirban,Karthika, Ardra,Rasappan, Ramesh. "C-H Alkylation of Aldehydes by Merging TBADT Hydrogen Atom Transfer with Nickel Catalysis". supporting information. p. 5389 - 5393. Retrieved 2021/07/21.