Sodium triacetoxyborohydride → 1H-Pyrrolo[2,3-b]pyridine-1,3-dicarboxylic acid, 4-[[[(1R)-1-(1-pyrrolidinylcarbonyl)propyl]amino]methyl]-, 1-(1,1-dimethylethyl) 3-methyl ester

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Reaction Steps

A mixture of sodium triacetoxyborohydride (237 mg, 1.116 mmol) and (R)-2-amino-1-(pyrrolidin-1-yl)butan-1-one (131 mg, 0.837 mmol) in DCE (2 mL) was stirred at room temperature for 30 min. The reaction mixture was cooled to 0° C. A solution of 1-tert-butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate (200 mg, 0.657 mmol) in DCE (2 mL) was added, followed by acetic acid (1 drop). The reaction was stirred at 0° C. for 30 min and then at room temperature for 3 h. Purification by silica column chromatography (EtOAc/DCM, 0-10%) afforded the title compound as a yellow oil (260 mg, 93%). [M+H] calc'd for C23H32N4O5, 445; found, 445.5.

Provenance & Evidence