Sodium Hydroxide → HCID 69654803, compound

Participants

Reaction Steps

To a slurry of added (2S,3S)-2-Phenyl-piperidin-3-ylamine dimalonate (1.26 g, 2.6 mmol) and 6-Methoxy-1-methyl-2-oxo-2,3-dihydro-1H-indole-5-carbaldehyde in 15 mL CH2Cl2 was added sodium triacetoxyborohydride (1.01 g, 4.8 mmol) in one portion. After 30 minutes the mixture was diluted with 10 mL of water and then basified with 3 N NaOH to a pH of ca. 11. The layers were separated and the aqueous portion was extracted once with CH2Cl2. The combined organic material was washed successively with 1 N NaOH and water, and was then dried with Na2SO4 and concentrated. Silica gel chromatography (90:9:1 EtOAc/MeOH/NH4OH) gave 127 mg (14%) of the title compound as a white solid. Mass spectrum m/e calcd for M+H=366.2. Found 366.0. The solid dihydrochloride salt was generated by treatment with excess HCl in ether followed by concentration in vacuo.

Provenance & Evidence