6-Aminohexanoic Acid → HCID 58636712, compound

Participants

Reaction Steps

A mixture of pyridoxal (20.0 g, 98.5 mmol) and 6-aminocaproic acid (22.2 g, 169 mmol) was stirred in methyl alcohol (2 L) at room temperature for 12 hours. The solution was placed in an ice bath and sodium borohydride (5.7 g, 167 mmol) was added slowly. The resulting mixture was stirred for one hour at room temperature and then the solvent was evaporated to dryness. The crude product was purified by column chromatography on silica gel using a mixture of dichloromethane:methyl alcohol:30% ammonium hydroxide (5:5:1) to give 6-[(3-hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-ylmethyl)-amino]hexanoic acid (40) (11.3 g, 41% yield) as colorless crystals.

Provenance & Evidence