1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal → 2-{4-[[1-(3-Methyl-pyridin-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione

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Reaction Steps

To a solution of the above amine and 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyraldehyde (127 mg, 0.58 mmol) in CH2Cl2 (2.5 mL) was added NaBH(OAc)3 (117 mg, 0.55 mmol) and the reaction was stirred at room temperature under N2 for 16 hours. The mixture was diluted with saturated aqueous NaHCO3 (10 mL) and was extracted with CH2Cl2 (10 mL×3). The combined organic solution was dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (CH2Cl2/MeOH, 9:1) gave 2-{4-[[1-(3-methyl-pyridin-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione as a 1:1 mixture of two diastereomers (72 mg, 0.15 mmol, 43%) along with some single diastereomer (33 mg, 0.07 mmol, 20%).

Provenance & Evidence