Acetic Acid → HCID 54191233, compound

Participants

Reaction Steps

A solution of 3-(6-bromo-pyridin-2-yl)propylamine 20-4 (25.6 g, 89.1 mmol), diisopropylethylamine (46.5 mL, 267 mmol), acetic acid (28 mL, 490 mmol), and ethyl glyoxylate (10.9 g, 107 mmol) in 200 ml of methanol was stirred at room temperature for one hour. A 1M solution of NaCNBH3 in THF (98.0 mL, 98.0 mmol) was added slowly with a syringe pump over 4 hours. The resulting solution was stirred for 12 hours, after which the solvent was removed in vacuo and the residue taken up in chloroform and filtered. The solution was then washed with 10% Na2CO3, dried over Na2SO4, and the solvent removed in vacuo to give the crude amine. The crude product was purified by silica gel chromatography (7% MeOH/CHCl3) to give 20-5 in a 3:2 mixture of ethyl and methyl esters.

Provenance & Evidence