Carbon Dioxide → (S)-2-amino-4-methylpentane-1,4-diol

Participants

Reaction Steps

A mixture of (4S)-4-(2-hydroxy-2-methylpropyl)-1,3-oxazolidin-2-one (1.0 g, 6.28 mmol), barium hydroxide (3.2 g, 18.8 mmol), ethanol (50 mL) and water (50 mL) was heated to reflux for 4 hours. See Gauthier et al., 2008, Bioorg. Med. Chem. Lett., 18:923-928. After cooling, dry ice (5.5 g, 125.6 mmol) was added and the mixture was stirred vigorously overnight. The suspension was then filtered over CELITE®, rinsing with ethanol. The filtrate was diluted with toluene and evaporated to dryness, yielding crude (S)-2-amino-4-methylpentane-1,4-diol (0.7 g) which was used without further purification in the next step.

Provenance & Evidence