2,6-Lutidine → HCID 60153206, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-methyl 2-((tert-butoxycarbonyl)amino)-4-methylpent-4-enoate (500 mg, 2.055 mmol) in a solvent mixture of 1,4-dioxane (10 mL) and water (2.5 mL) at 0° C., was added 2,6-lutidine (0.479 mL, 4.11 mmol) and osmium tetroxide (2.5% in 2-methyl-2-propanol) (0.516 mL, 0.041 mmol), followed by sodium metaperiodate (1.758 g, 8.22 mmol). The reaction mixture was stirred at 0° C. for 15 min and warmed to room temperature and stirred for an additional 3 h. The mixture was diluted with ethyl acetate (150 mL) and washed with 10% aqueous NaHCO3. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure to afford (S)-methyl 2-((tert-butoxycarbonyl)amino)-4-oxopentanoate (500 mg, 2.040 mmol, 100% crude yield) as a yellow liquid. The material was carried on without further purification. 1H NMR (400 MHz, CDCl3): δ ppm 5.48 (s, 1H), 4.51 (t, J=8.00 Hz, 1H), 3.75 (s, 3H), 3.23 (d, J=4.00 Hz, 1H), 3.17 (d, J=4.00 Hz, 1H), 2.18 (s, 3H), 1.46 (s, 9H).

Provenance & Evidence