1,4-Bis(dihydroquinidine)phthalazine → HCID 57456807, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of AD-mix-beta (34 g) in t-BuOH—H2O (1:1, 0.077 M) at 0° C., was added hex-5-en-1-yl 4-nitrobenzoate (6 g, 24.07 mmol). The reaction was stirred at 0° C. overnight. The reaction mixture was diluted with 250 mL of EA, quenched by addition of 10 g of sodium metabisulfite and stirred 30 min at 0° C. The mixture was allowed to stir at rt for 1 h then was extracted 3 times with EtOAc, washed with brine, dried over Na2SO4, filtered and evaporated. The compound was recrystallized with ether and stirred in the cold room overnight for twice to afford 3.3 g of the titled compound as a white solid (greater than 99% in e.e. by Mosher derivatives analysis). 1H NMR (500 MHz, acetone-d6): δ 8.36 (d, 2H), 8.27 (d, 2H), 4.38 (t, 2H), 3.62-3.54 (m, 3H), 3.49-3.45 (m, 1H), 3.41-3.35 (m, 1H), 1.87-1.77 (m, 2H), 1.69-1.62 (m, 1H), 1.59-1.49 (m, 2H), 1.46-1.40 (m, 1H).

Provenance & Evidence