Acetic Acid → HCID 54670022, compound

Participants

Reaction Steps

Sodium triacetoxyborohydride (200 mg, 0.944 mmol) was added to an ice-cooled solution of 4-bromobenzaldehyde (122 mg, 0.659 mmol) and the product of Example 22F (63 mg, 0.290 mmol) in tetrahydrofuran (5 mL). A few drops of 10% HCl (aq) were added, and the mixture was allowed to warm to room temperature. After 5 hours, acetic acid (2 mL) and additional sodium triacetoxyborohydride (200 mg, 0.944 mmol) were added, and the mixture was stirred an additional 15 hours. The reaction mixture was concentrated under vacuum, and the residue was purified by flash chromatography (SiO2, eluted with CH2Cl2, then CH2Cl2-methanol-15 M NH4OH, 95:5:0.5-90:10:1) to provide the title compound: 1H NMR (300 MHz, CD3OD) δ ppm 1.62 (tt, J=15.3, 5.3, 2.6 Hz, 1H), 1.84-2.00 (m, 1H), 2.33 (t, J=10.9 Hz, 1H), 2.42-2.51 (m, 1H), 2.43 (s, 3H), 2.77 (dt, J=10.7, 2.0 Hz, 1H), 2.85 (ddd, J=11.1, 5.2, 3.6 Hz, 1H), 2.89-3.04 (m, 2H), 3.13 (dt, J=11.9, 2.8 Hz, 1H), 3.30 (s, 1H), 3.45 (td, J=11.3, 2.8 Hz, 1H), 4.22 (d, J=15.1 Hz, 1H), 4.46 (d, J=15.1 Hz, 1H), 6.77-6.96 (m, 4H), 7.27 (d, J=8.3 Hz, 2H), 7.44 (d, J=8.3 Hz, 2H); MS (DCI) m/z 386/388 (M+H)+.

Provenance & Evidence