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ChemicalBook CAS DataBase List tert-Butyl 1-(3-nitrobenzyl)piperidin-4-ylcarbamate
323578-32-1

tert-Butyl 1-(3-nitrobenzyl)piperidin-4-ylcarbamate synthesis

3synthesis methods
-

Yield:323578-32-1 76%

Reaction Conditions:

with sodium tris(acetoxy)borohydride;acetic acid in methanol at 30;

Steps:



To a mixture of tert-butyl N-(piperidin-4-yl)carbamate (25 g, 125 mmol, 1.0 eq) and 3- nitrobenzaldehyde (19 g, 125 mmol, 1.0 eq) in MeOH (500 mL) were added NaBH(OAc)3 (53 g, 250 mmol, 2.0 eq) and acetic acid (1 mL). Then the resulting mixture was stirred at 30°C overnight. LC-MS indicated complete conversion. The solvent was removed under vaccum and the residue was purified by column chromatography (DCM: MeOH = 15:1), to provide tert-butyl N-{1-(3- nitrobenzyl)piperidin-4-yl}carbamate (32 g, 76%) as a white solid.

References:

WO2014/68035,2014,A1 Location in patent:Page/Page column 38