Diisopropylethylamine → tert-butyl (3R,4R,5S)-4-(tert-butyldimethylsilyloxy)-5-methyl-1-(3-nitropyridin-4-yl)piperidin-3-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-3-nitropyridine (96.6 mg, 0.609 mmol), tert-butyl ((3R,4R,5S)-4-{[tert-butyl(dimethyl)silyl]oxy}-5-methylpiperidin-3-yl)carbamate (300 mg, 0.609 mmol) and DIPEA (0.319 mL, 1.83 mmol) in isopropyl alcohol (20 mL) was stirred at 100° C. for 4 h. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by flash chromatography on silica using a CombiFlash® apparatus (eluting with 0 to 30% EtOAc in hexanes) to give the sub-title compound as a pale yellow powder (1.93 g). LCMS calc. for C22H39N4O5Si (M+H)+: m/z=467.3. found: 467.1.

Provenance & Evidence