Acetic Acid → HCID 70873974, compound

Participants

Reaction Steps

To a solution of methyl 5-chloro-2-ethyl-3-[(oxan-4-yl)amino]benzoate (350 mg, 1.18 mmol) in 1,2-dichloroethane (10 ml) at room temperature under nitrogen was added acetaldehyde (0.66 ml, 11.8 mmol) followed by acetic acid (0.4 ml, 7.05 mmol). This solution was stirred for 5 minutes before the addition of sodium triacetoxyborohydride (2.49 g, 11.8 mmol) at room temperature. After stirring for 23 hours acetaldehyde (0.66 ml, 11.8 mmol) was added to the dark reaction mixture and this was stirred for 10 minutes before the addition of sodium triacetoxyborohydride (2.49 g, 11.8 mmol). After stirring for 3 hours deionized water (15 ml) was added and the mixture was neutralized with solid NaHCO3. The phases were separated and the aqueous layer was extracted with EtOAc (2×15 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by FCC (10 g silica, Isolute cartridge, gradient of eluents; 99:1 Heptane:EtOAc to 85:15 Heptane:EtOAc) to give 317 mg of the title compound as a colorless oil. The product contains ˜25% ether ester. The material was taken through the next step without further purification. LC-MS 55%, 2 m/z=326.0/328.0, 1H NMR (500 MHz, Chloroform-d) δ ppm 7.52 (d, J=2.2 Hz, 1H), 7.23 (d, J=2.2 Hz, 1H), 3.97 (d, J=11.1 Hz, 2H), 3.90 (s, 3H), 3.32 (td, J=11.6, 2.5 Hz, 2H), 3.04 (q, J=7.1 Hz, 4H), 2.93 (ddd, J=15.1, 10.8, 4.3 Hz, 1H), 1.76-1.62 (m, 4H), 1.08 (t, J=7.4 Hz, 3H), 0.88 (t, J=7.1 Hz, 3H).

Provenance & Evidence