4-(TOLUENE-4-SULFONYLOXY)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties

Melting point:

96.0 to 100.0 °C

Boiling point:

475.3±38.0 °C(Predicted)

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

-2.97±0.40(Predicted)

color 

White to Almost white

InChI

InChI=1S/C17H25NO5S/c1-13-5-7-15(8-6-13)24(20,21)23-14-9-11-18(12-10-14)16(19)22-17(2,3)4/h5-8,14H,9-12H2,1-4H3

InChIKey

IKOMRHLHPZAEMV-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(OS(C2=CC=C(C)C=C2)(=O)=O)CC1

Safety Information

HS Code 

2933399990

4-(TOLUENE-4-SULFONYLOXY)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Usage And Synthesis

Synthesis

To a solution of N-Boc-4-hydroxypiperidine (5 g, 24.8 mmol) in dichloromethane (50 mL) was sequentially added triethylamine (13.9 mL, 99.4 mmol) and p-toluenesulfonyl chloride (9.47 g, 49.7 mmol). The reaction mixture was stirred at room temperature for 20 hours. Upon completion of the reaction, the solution was concentrated in vacuum. The residue was redissolved in a mixture of dichloromethane (20 mL) and water (20 mL) and the organic layer was extracted with dichloromethane (20 mL). Subsequently, the organic layer was washed with 1N HCl (40 mL) and extracted twice more with dichloromethane (2 x 40 mL). The organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated. Finally, the crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 8:2) to afford tert-butyl 4-(toluene-4-sulfonyloxy)piperidine-1-carboxylate (8.7 g, quantitative yield) as a white crystalline solid.

References

[1] Patent: WO2018/50771, 2018, A1. Location in patent: Page/Page column 72
[2] Patent: WO2007/102883, 2007, A2. Location in patent: Page/Page column 36-37
[3] Patent: WO2013/170072, 2013, A2. Location in patent: Paragraph 001074
[4] Patent: WO2007/30366, 2007, A1. Location in patent: Page/Page column 135
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9958 - 9972

4-(TOLUENE-4-SULFONYLOXY)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER (118811-07-7)Related Product Information

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