Sodium t-butoxide → HCID 54591155, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(6-bromo-2-methyl-pyridin-3-yl)-1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester (0.09 g, 0.211 mmol), (2S,3′S)-2-methyl-[1,3′]bipyrrolidinyl (0.065 g, 0.422 mmol), R-(−)-BINAP (0.01 g, 0.016 mmol), and anhydrous toluene (3 mL) was de-gassed and refilled with N2 in three cycles. Pd2(dba)3 (0.005 g, 0.0053 mmol,), and sodium t-butoxide (0.030 g, 0.317 mmol) was then added to the mixture and de-gassed and refilled with N2 in three additional cycles. The reaction mixture was heated and stirred at 90° C. for 16 hours. The reaction mixture was allowed to cool to room temperature and quenched with water (1 mL). The aqueous phase was extracted with dichloromethane (3×10 mL). The combined organics were washed with sodium bicarbonate (5 mL), and brine (10 mL), dried over Na2SO4, concentrated under vacuum. Purification by column chromatography on silica gel (0-10%) methanol in dichloromethane afforded 0.0599 g (57%) of title compound.

Provenance & Evidence