Triethylamine → Ammonium Hydroxide

Participants

Reaction Steps

To a cooled (0° C.) solution of (2R)-5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (0.100 g, 0.398 mmol, Intermediate 9) and triethylamine (100. μL, 0.716 mmol) in THF (8 mL) was added bromoacetyl bromide (46.0 μL, 0.523 mmol). After allowing the reaction to warm to ambient temperature, triethylamine (0.230 mL, 1.67 mmol) and methyl 1-{[(3S)-3-amino-3-phenylpropyl]amino}cyclopentanecarboxylate bis-hydrochloride (0.139 g, 0.398 mmol, Intermediate 38) were added, prior to heating the reaction to 50° C. for 17 h. After cooling to ambient temperature, the reaction mixture was diluted with chloroform and saturated aqueous sodium bicarbonate. The aqueous layer was extracted twice with additional chloroform. The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to give an oil. This oil was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH:NH4OH—99:1:0.1 to 92:8:0.8, to give the title compound. MS: m/z=568 (M+1).

Provenance & Evidence