Acetone → HCID 46888080, compound

Participants

Reaction Steps

To a solution of (2R,4S)-1-[2-([1,4]diazepane-1-carbonyl)-4-(3-fluoro-phenoxy)-pyrrolidin-1-yl]-ethanone (220 mg, 0.63 mmol) in dichloroethane (3 mL) was added acetone (324 μL, 4.41 mmol) and sodium triacetoxyborohydride (199 mg, 0.945 mmol). After 2 days, the reaction mixture was diluted with satd. aq. NaHCO3 and extracted with CH2Cl2 (4×). The combined organic layers were dried and concentrated. Purification of the residue by FCC provided the desired product (205 mg, 83%). MS (ESI): mass calcd. for C21H30FN3O3, 391.23; m/z found, 392.3 [M+H]+. 1H NMR (CDCl3): 7.22 (ddd, J=8.3, 8.3, 6.9 Hz, 1H), 6.69-6.64 (m, 1H), 6.63 (dd, J=8.3, 2.3 Hz, 1H), 6.57 (ddd, J=10.6, 2.2, 2.2 Hz, 1H), 5.09-5.03 (m, 1H), 5.00-4.95 (m, 1H), 4.03 (dd, J=11.1, 4.9 Hz, 1H), 3.74-3.59 (m, 4H), 3.55-3.45 (m, 1H), 2.92-2.78 (m, 1H), 2.75-2.51 (m, 4H), 2.40-2.23 (m, 2H), 2.04 (s, 3H), 2.01-1.92 (m, 1H), 1.85-1.67 (m, 1H), 1.00-0.94 (m, 6H).

Provenance & Evidence