Diisopropylethylamine → HCID 58550625, compound

Participants

Reaction Steps

To a stirred suspension of methyl-{[(3S)-3-amino-3-phenylpropyl]amino}cyclopentanecarboxylate dihydrochloride (222 mg, 0.634 mmol, prepared according to U.S. Patent Application Publication No. US 2007/0265225) and (7S)-2′-oxo-1′,2′, 6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridine]-3-carbaldehyde (200 mg, 0.634 mmol, Intermediate 1) in chloroform (16 mL) was added Hunig's base (0.222 mL, 1.27 mmol). One hour later, sodium triacetoxyborohydride (403 mg, 1.90 mmol) was added. Two hours later, the reaction was quenched by the addition of saturated sodium bicarbonate (3 mL) and the reaction was allowed to stir for an additional 30 minutes. This mixture was further diluted with water (10 mL) and chloroform (40 mL). The aqueous layer was separated and extracted once with chloroform (30 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue. This residue was applied to a silica gel column for purification, eluting with a gradient of CH2Cl2:MeOH (10% conc. NH4OH)—99:1 to 90:10. Clean product-containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=576 (M+1).

Provenance & Evidence