Acetaldehyde → HCID 178448301, compound

Participants

Reaction Steps

To (a) (S)-6-{trans-4-[1-(4-fluorophenylsulfanyl)pentan-2-ylamino]cyclohexyl}-3H-benzoxazol-2-one (292 mg, 0.687 mmol) in THF (10 mL) was added acetaldehyde (30 mg, 0.68 mmol) and 4 Å molecular sieves. After stirring for 0.25 hours, sodium triacetoxyborohydride (204 mg, 0.962 mmol) was added. The reaction mixture was stirred for 0.75 hours then concentrated under reduced pressure. The crude residue was taken up in methanol (10 mL), and solid NaOH was added until the pH was >8. The solution was concentrated under reduced pressure. Purification by flash chromatography (silica, 1:1 Hexanes:EtOAc) gave (b) (S)-6-{trans-4-[ethyl(1-(4-fluorophenylsulfanyl)-pentan-2-yl)amino]cyclohexyl}-3H-benzoxazol-2-one (210 mg, 67%), as a clear oil: IR (KBr): 3219, 2926, 1764, 1589 cm−1; 1H NMR (500 MHz, CDCl3): δ 7.34 (m, 2H), 7.05-6.92 (m, 5H), 3.02 (m, 3H), 2.79 (m, 1H), 2.64 (m, 6H), 2.38 (m, 1H), 1.93-1.78 (m, 4H), 1.47-1.29 (m, 4H), 0.93 (t, J=5 Hz, 3H), 0.89 (t, J=6 Hz, 3H); API-MS (m/z): 457 [M+H]+; calcd for C26H33FN2O2S, 457.2325; found, 457.2324; HPLC: method C, 6.55 minutes (>99%), method D, 12.37 minutes (>99%).

Provenance & Evidence