Acetic Acid → HCID 86699924, compound

Participants

Reaction Conditions

Reaction Steps

In a round bottomed flask equipped with a magnetic stirrer (4-methyltetrahydropyran-4-yl)-N-aminocarbamate (0.540 g, 3.10 mmol), H2O (10 mL) and CH3COOH (0.35 mL, 6.20 mmol) were sequentially added. The resulting mixture was cooled to 0° C. and NaNO2 (0.354 g, 3.72 mmol) dissolved in H2O (2 mL) was added dropwise. The cloudy mixture was stirred for 1.5 h at rt. Dioxane (20 mL) followed by the D-threonine salt solution [prepared from D-threonine (0.554 g, 4.65 mmol) solution in H2O (4 mL) and Na2CO3 (1.34 g, 12.40 mmol)] were added to the mixture. After being left overnight at 45° C., the crude mixture was then cooled to rt, then H2O (30 mL) and AcOEt (80 mL) were added and, while maintaining a vigorous stirring, the pH was adjusted to 2 with 2M HCl solution. The phases were separated and the aqueous one washed with AcOEt (2×50 mL). The combined organic liquors were dried over Na2SO4 and concentrated to leave a light yellow oil (0.647 g, 80%), which was used in the next step without purification. MS (ESI) m/z: 284.1 [M−Na]+. 1H NMR (DMSO-d6): δ 1.09 (d, J=6.3 Hz, 3H), 1.47 (s, 3H), 1.63 (m, 2H), 1.99 (m, 2H), 3.61 (m, 5H), 3.90 (dd, J=9.4, 6.3 Hz, 1H), 4.09 (m, 1H), 6.53 (d, J=9.4 Hz, 1H), 12.20 (bs, 1H).

Provenance & Evidence