Borohydride → HCID 57659379, compound

Participants

Reaction Conditions

Reaction Steps

Zn(BH4)2 was prepared following a known procedure (Beatrix Merla, Hans-Joachim Grumbach, Nikolaus Risch, Synthesis, 1998 1609-1614). At 0° C., zinc chloride (anhydrous, 5 g, 36.6 mmol) was added to a solution of sodium borohydride (2.72 g, 72 mmol) in diethyl ether (100 ml). The reaction mixture was stirred at 0° C. for 2 h. After filtration under N2, the borohydride solution (9 ml) was added to a suspension of the tert-butyl 3-(2-methoxy-2-oxoethyl)-4-oxo-3,4-dihydro-2H-spiro[naphthalene-1,4′-piperidine]-1′-carboxylate (589 mg, 1.52 mmol). After 1 h, additional borohydride solution (9 ml) was added and the mixture stirred for 15 h. The mixture was quenched with 1N HCl, neutralized with saturated sodium bicarbonate, extracted with EtOAc. The extract was concentrated and the residue purified by flash chromatography to give the title compound (140 mg).

Provenance & Evidence