158407-04-6

Basic information

• Product Name: 4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• Synonyms: 4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;1-N-BOC-4-BROMOMETHYLPIPERIDINE;1-BOC-4-BROMOMETHYLPIPERIDINE;4-Bromomethyl-piperidine-1-carboxylic acid tert-butyk ester;N-BOC-4-BROMOMETHYL-PIPERIDINE;tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate;4-Bromomethyl-1-(tert-butoxycarbonyl)piperidine;1-Piperidinecarboxylic acid, 4-(bromomethyl)-, 1,1-dimethylethyl ester
• CAS NO: 158407-04-6
• Molecular Formula: C₁₁H₂₀BrNO₂
• Molecular Weight: 278.19
• Product Categories: pharmacetical
• Mol File: 158407-04-6.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 318.337 °C at 760 mmHg
• Flash Point: 146.325 °C
• Appearance: /
• Density: 1.271 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.495
• Storage Temp.: Room temperature.
• PKA: -1.91±0.40(Predicted)
• CAS DataBase Reference: 4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(158407-04-6)
• EPA Substance Registry System: 4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(158407-04-6)

Safety Data

• Statements: 36/37/38-36
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 158407-04-6(Hazardous Substances Data)

Usage

Uses

4-Bromomethypiperidine-1-carboxylic acid tert-butyl ester can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly in laboratory research and development process and chemical production process.

Synthesis

4-Bromomethypiperidine-1-carboxylic acid tert-butyl ester. 4-N-Boc-piperidine-methanol (200 mg, 0.93 mmol) was dissolved in diethyl ether (9 mL) and carbon tetrabromide (370 mg, 1.1 mmol) and PPh3 (292 mg, 1.1 mmol) were added at rt. The reaction was allowed to stir for 18 h at rt and filtered over a pad of celite. The filtrate was concentrated and purified by flash chromatography (hexane/EtOAc, 1:0 → 4:1) to give the title compound. Yield 55 mg. 1 (400 MHz, DMSO-d6) δ ppm 4.02-3.98 (m, 2 H), 3.47 (d, 2 H), 2.78-2.65 (m, 2 H), 1.89-1.74 (m, 3 H), 1.45 (s, 9 H), 1.12-0.98 (m, 2 H).

InChI:InChI=1/C11H20BrNO2/c1-11(2,3)15-10(14)13-6-4-9(8-12)5-7-13/h9H,4-8H2,1-3H3

Upstream product

• 69719-84-2 4-(bromomethyl)piperidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 6457-49-4 4-piperidinemethanol 
• 161975-39-9 tert-butyl 4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 498-94-2 isonipecotic acid 
• 123855-51-6 tert-butyl 4-(hydroxymethyl)piperidin-1-carboxylate 

Downstream Products

• 1264296-64-1 tert-butyl 4-(2-(3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl)-3-ethoxy-2-methyl-3-oxopropyl)piperidine-1-carboxylate 
• 912482-43-0 1-(4-(bromomethyl)piperidin-1-yl)ethan-1-one 

Relevant articles and documents

Structural requirements for TLR7-selective signaling by 9-(4-piperidinylalkyl)-8-oxoadenine derivatives

We report the synthesis and biological evaluation of a new series of 8-oxoadenines substituted at the 9-position with a 4-piperidinylalkyl moiety. In vitro evaluation of the piperidinyl-substituted oxoadenines 3a-g in human TLR7- or TLR8-transfected HEK293 cells and in human PBMCs indicated that TLR7/8 selectivity/potency and cytokine induction can be modulated by varying the length of the alkyl linker. Oxoadenine 3f containing a 5-carbon linker was found to be the most potent TLR7 agonist and IFNα inducer in the series whereas 3b possessing a 1-carbon linker was the most potent TLR8 agonist.

Compound with dual inhibitory activity TDO, IDOO1 and application of compound for treating neurodegenerative disease (by machine translation)

The present invention provides a compound of formula I, or a pharmaceutically acceptable salt thereof, or a solvate thereof, which can selectively inhibit TDO, IDOO1, which has a significant inhibitory effect on TDO and/or IDOO1. In addition, the prepared compound has a remarkable anti-tumor effect, has a certain treatment effect on's disease and's disease, and has a good application prospect in the field of medicine preparation. (by machine translation)

Anodic oxidation of dithiane carboxylic acids: A rapid and mild way to access functionalized orthoesters

A new electrochemical methodology has been developed for the preparation of a wide variety of functionalized orthoesters under mild and green conditions from easily accessible dithiane derivatives. The new methodology also offers an unprecedented way to access tri(fluorinated) orthoesters, a class of compound that has never been studied before. This provides the community with a rapid and general method to prepare libraries of functionalized orthoesters from simple and readily available starting materials.