Sodium hydride → HCID 21093755, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2-methoxy-3-nitrobenzyl bromide (8.4 9, 26 mmol) and triethyl phosphite (4.5 g, 27 mmol) was heated to 160° C. for 2 h and then evaporated in vacuo to give a dark amber oil. This was dissolved in anhydrous tetrahydrofuran (20 mL) and added dropwise to a stirring suspension of sodium hydride (60%) (1.14 g) in anhydrous N,N-dimethylformamide (100 mL) at 0° C. The mixture was left to stir for 1 hour. tert-Butyl 4-oxopiperidine-1-carboxylate (5.17 g, 26 mmol) in anhydrous THF (30 mL) was added to the mixture. Stirring was continued for 4 h at room temperature before the mixture was poured into saturated ammonium chloride (100 mL) and extracted with diethyl ether (2×150 mL). The combined organic layer was evaporated in vacuo to give a crude oil. Silica gel chromatography eluting with diethyl ether in petroleum ether (5–30%) gave the title compound (3.9 g, 35%) as an oil.

Provenance & Evidence