3-BROMO-4-OXO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties

Boiling point:

333.3±42.0 °C(Predicted)

Density 

1.422±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

solid

pka

-3.35±0.40(Predicted)

color 

White

InChI

InChI=1S/C10H16BrNO3/c1-10(2,3)15-9(14)12-5-4-8(13)7(11)6-12/h7H,4-6H2,1-3H3

InChIKey

RGWGRRBHQUREDE-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(=O)C(Br)C1

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

3-BROMO-4-OXO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Usage And Synthesis

Uses

3-Bromo-4-oxopiperidin-1-carboxylic acid tert-butyl ester is an ester organic compound that can be used as an organic intermediate.

General Description

3-Bromo-4-oxopiperidine-1-carboxylic acid tert-butyl ester is a colorless liquid that is soluble in organic solvents. It can be prepared by reacting lithium metal with carbon dioxide and bromine in an ethereal solvent, followed by reaction with tert-butyl alcohol.

Synthesis

The general procedure for the synthesis of N-Boc-3-bromo-4-oxopiperidine from N-Boc-4-piperidone was as follows: 1. triethylamine (TEA, 7.7 mL, 55 mmol) and trimethylchlorosilane (TMSCl, 3.5 mL, 27.6 mmol) were sequentially added to a solution of N,N-dimethylformamide (DMF, 30 mL) containing tert-butyl 4-oxopiperidine-1-carboxylate (5 g, 25 mmol) at room temperature. 2. The reaction mixture was stirred at 75 °C overnight. 3. After completion of the reaction, the reaction solution was cooled to room temperature and pre-cooled saturated aqueous sodium bicarbonate (200 mL) and hexane (200 mL) were added sequentially. 4. Separate the organic phase, wash it with saturated aqueous sodium chloride solution, and subsequently dry and concentrate it with anhydrous sodium sulfate to obtain a crude product, which was directly used in the next step of the reaction. 5. The above crude product was dissolved in tetrahydrofuran (THF, 15 mL) and stirred at 0 °C for 15 min. 6. A solution of N-bromosuccinimide (NBS, 4.47 g, 25 mmol) dissolved in THF (80 mL) was slowly added dropwise to the above reaction solution. 7. After the dropwise addition, the reaction mixture was stirred at room temperature overnight. 8. At the end of the reaction, water (200 mL) and hexane (200 mL) were added to the reaction solution. 9. The organic phase was separated, washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. 10. The crude product was purified by silica gel column chromatography (60 g of silica gel, gradient elution of petroleum ether/ethyl acetate=20/1 to 8/1) to afford tert-butyl 3-bromo-4-oxopiperidine-1-carboxylate as a white solid (5.56 g, 78% yield).

References

[1] ChemMedChem, 2012, vol. 7, # 12, p. 2087 - 2092
[2] Patent: TWI602818, 2017, B. Location in patent: Paragraph 0424; 0425
[3] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 23-24, p. 5987 - 5999
[4] Patent: US6599895, 2003, B1
[5] Patent: EP1801108, 2007, A1. Location in patent: Page/Page column 56

3-BROMO-4-OXO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(188869-05-8)Related Product Information

• tert-butyl (4-bromobutyl)carbamate
• CIS-2-HYDROXY-1-CYCLOPENTANECARBOXYLIC ACID,99%
• 3-BROMO-4-OXO-PIPERIDINE-1-CARBOXYLIC ACID ETHYL ESTER
• tert-Butyl N-(2-bromoethyl)carbamate
• 3-BROMOPIPERIDINE
• 1-N-BOC-3-BROMOPIPERIDINE
• 3-BROMO-4-OXO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER