Ethanol → HCID 69032049, compound

Participants

Reaction Conditions

Reaction Steps

EtOH (900 ml) and MeOH (90 ml) were added to a 2 L flask. Powdered sodium borohydride (20.5 g, 0.55 mol) was then added. The suspension was cooled to 15° C. Nitroalkene 12 (49.0 g, 0.11 mol) was added in portions over 45 minutes while the temperature was maintained at ˜15° C. After addition was complete, additional EtOH (800 ml) was added. The reaction mixture was stirred for 15 minutes. TLC analysis indicated the completion of the reaction. A mixture of acetic acid (40 ml) and water (40 ml) was added slowly to quench the excess of sodium borohydride. A reddish suspension was obtained. Solvent was removed in a rotovap. The residue was partitioned between EtOAc (600 ml) and water (300 ml). Aqueous phase was separated. The solid in organic layer was collected by filtration and dried to afford 21.94 g of product 13 (45% yield). The organic filtrate was concentrated to dryness. The residue was then reslurried with EtOAC (70 ml)/heptane (200 ml). The solid was collected by filtration and dried to afford second crop of product (21.74 g, 44% yield). The combined yield for this step is 89%. 1H NMR (300 MHz, DMSO-d6) δ 2.87 (s, 3H), 3.584 (t, 2H, J=7.8 Hz), 3.661 (s, 3H), 3.903 (s, 3H), 4.519 (s, 2H), 4.607 (t, 2H, J=7.8 Hz), 7.41 (m, 4H), 7.58 (d, 2H, J=8.10 Hz), 12.0 (s, br, 1H). Exact mass calculated for C22H23FN3O6: 444.1571. Found: 444.1559.

Provenance & Evidence