Sodium hydride → Rac-(3R*,4R*)-tert-butyl 4-(((2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)amino)methyl)-3-hydroxypiperidine-1-carboxylate

Participants

Reaction Steps

A mixture of rac-(3R*,4R*)-tert-butyl 3-hydroxy-4-((tosyloxy)methyl)piperidine-1-carboxylate (prepared as described in Tetrahedron (2008), 64, 2456-2464, 0.26 g, 0.67 mmol) and tert-butyl (2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)carbamate (prepared as described in WO 2009/104159, 0.17 g, 0.67 mmol, 1 eq.) was dissolved in DMF (2.5 mL). NaH (60% dispersion in oil, 0.04 g, 0.88 mmol, 1.3 eq.) was added and the mixture was vigorously stirred at rt for 2 h. More NaH (0.03 g, 0.67 mmol, 1 eq.) was added. After two more hours, sat. aq. NaHCO3 (5 mL) was added and the mixture was extracted with EA (3×10 mL). The combined org. phases were dried over MgSO4 and concentrated under reduced pressure. The residue was purified by CC (DCM/MeOH 19:1) to afford the title compound as a white solid (0.15 g, 62% yield).

Provenance & Evidence