Sodium triacetoxyborohydride → HCID 56599194, compound

Participants

Reaction Steps

To a solution of 4-(1-(5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde (0.55 g, 1.45 mmol in DCM (30 mL) were added (4-ethylpiperidin-4-yl)methanol (0.27 g, 1.88 mmol, 1.3 equiv) and sodium triacetoxyborohydride (0.615 g, 2.90 mmol, 2 equiv). The reaction mixture was stirred at room temperature overnight and thereafter transferred to a reparatory funnel, washed with a saturated solution of Na2CO3, dried (phase separator) and concentrated under reduced pressure. The crude product was purified by automatic flash column chromatography using Biotage (eluting with EtOAc (10 CV), then EtOAc/MeOH (containing 2 M NH3) 20:1) on a 50 g snap column, collecting at UV 291 nm). The pure product fractions were combined and evaporated to afford the product as a white solid. Recrystallisation from DCM/Et2O afforded 280 mg, 38% of the product as a white solid (purity >99%). 1H NMR (400 MHz, CDCl3): δ 0.82 (t, 3H), 1.37-1.56 (m, 6H), 2.30-2.46 (m, 4H), 3.45 (2×s, 4H), 3.89 (s, 3H), 4.33 (dd, 1H), 4.64 (dd, 1H), 4.74 (dd, 1H), 5.03-5.15 (m, 2H), 6.72 (d, 2H), 7.02 (d, 2H), 7.25 (d, 2H), 8.1 (d, 2H), MS (APCI+) m/z 507 [M+H]+.

Provenance & Evidence