D-Threonine → HCID 86699926, compound

Participants

Reaction Steps

In a round bottom flask, NaHCO3 (1.78 g, 21.2 mmol) was suspended in THF (4.5 mL) and H2O (9 mL), then D-threonine was added (1.0 g, 8.39 mmol). Tricyclo[3.3.1.13,7]dec-1-yl chlorocarbonate (2.0 g, 9.33 mmol) was added slowly, followed by a catalytic amount (0.1 g) of tetrabutylamonium bromide. After stirring 18 h at rt, the mixture was diluted with water, washed twice with Et2O and pH of aqueous phase adjusted to 2 with 2M HCl solution. The aqueous phase was extracted four times with AcOEt, the collected organic phases were dried over Na2SO4, filtered, and the solvent removed under vacuum to give the title compound (0.250 g, 10%) as white solid. Rf=0.38 (AcOEt+1% CH3COOH, detection: ninhydrin). FTIR (cm−1): 3421, 2911, 2852, 1718, 1509, 1254, 1068.

Provenance & Evidence