ChemicalBook CAS DataBase List 4-(TOLUENE-4-SULFONYLOXY)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

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

7synthesis methods

Product Name:4-(TOLUENE-4-SULFONYLOXY)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
CAS Number:118811-07-7
Molecular formula:C17H25NO5S
Molecular Weight:355.45

98-59-9

109384-19-2

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

118811-07-7

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.

98-59-9 Synthesis

98-59-9
625 suppliers
$9.00/5g

109384-19-2 Synthesis

109384-19-2
384 suppliers
$5.00/1g

118811-07-7
117 suppliers
$9.00/250mg

Yield: 100%

Reaction Conditions:

with triethylamine in dichloromethane at 20; for 20 h;

Steps:

61.5 Synthesis of compound (34) 1-(tert-butoxycarbonyl)-4-(p-toluensulfonyloxy)- piperidine
To a solution of compound (33) (5 g, 1 eq., 24.8 mmol) in dichloromethane (50 mL) wasadded triethylamine (13.9 mL, 4 eq., 99.4 mmol) and p-toluenesulfonyl chloride (9.47 g, 2eq., 49.7 mmol). The solution was stirred for 20h at room temperature followed by the concentration of this solution in vacuo. The residue was then dissolved in dichloromethane (20 mL) and water (20 mL), extracted with DCM (20 mL), washed with 1 N HCl (40 mL), extracted twice with DCM (2 x 40 mL), dried over Mg504 andevaporated. The resulting mixture was then purified by silica gel column chromatography (Petroleum ether/EtOAc 8:2) and compound (34) was obtained as a white crystalline solid (8.7g, quantitative yield)

References:

CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE;UNIVERSITE D'ORLEANS;AGROFOGLIO, Luigi;ROY, Vincent;PLEBANEK, Elzbieta;BESSIERES, Maxime WO2018/50771, 2018, A1 Location in patent:Page/Page column 72

5382-30-9 Synthesis