Sodium triacetoxyborohydride → HCID 178509524, compound

Participants

Reaction Steps

To a solution of 0.170 g of 3-(3-fluoro-phenoxy)-azetidine in 10 mL of CH2Cl2 was added 0.180 g of 3-(4-oxo-cyclohexyl)-1H-indole-5-carbonitrile followed by 0.420 g of sodium triacetoxyborohydride. The reaction was stirred at room temperature overnight. It was quenched with 1N NaOH and the product was extracted with ether. The organic phase was washed with water, dried over magnesium sulfate, filtered, and concentrated. The product was filtered through 150 mL of silica gel using 50% ethyl acetate/hexane, 75% ethyl acetate/hexane and finally 100% ethyl acetate to give 0.095 g of the desired product: mp 187-190° C. 1H NMR (300 MHz, CDCl3) δ 1.51-1.65 (m, 2H), 1.69-1.75 (m, 4H), 1.77-1.90 (m, 2H), 2.45 (m, 1H), 2.90 (m, 1H), 3.03 (dd, 2H), 3.81 (dd, 2H), 4.77 (m, 1H), 6.53-6.59 (m, 2H), 6.66 (m, 1H), 7.13-7.22 (m, 2H), 7.39 (dd, 2H), 8.00 (s, 1H), 8.28 (s, 1H); MS (ES) m/z (relative intensity): 390 (M++H).

Provenance & Evidence