Cl.CN.[CH2:4]([N:6](CC)CC)C.C(O)(=O)C.[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]([CH2:25][CH:26]=[CH2:27])[CH:23]=O)[CH:19]=[CH:20][CH:21]=1.C([BH3-])#N.[Na+]>CO.C(OCC)(=O)C>[CH3:4][NH:6][CH2:23][CH:22]([C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([Cl:15])[CH:17]=1)[CH2:25][CH:26]=[CH2:27]Methylamine hydrochloride (595 mg, 8.81 mmol), triethylamine (1.23 mL, 893 mg, 8.82 mmol) and acetic acid (0.290 mL, 304 mg, 4.98 mmol) were added to a stirred solution of of 2-(3-chlorophenyl)pent-4-enal (350 mg, 1.80 mmol) in 8 mL of methanol at room temperature. After 10 min, sodium cyanoborohydride (97 mg, 1.6 mmol) was added and stirring was continued overnight. The mixture was then diluted with 100 mL of ethyl acetate and washed with a mixture of 30 mL of saturated sodium bicarbonate and 10 mL of brine, followed by 40 mL of brine. The organic layer was dried over sodium sulfate, decanted, and evaporated. The residue was partitioned between 25 mL of ethyl ether and 20 mL of 2.0 N aqueous HCl. The aqueous layer was washed with 25 mL of ethyl ether, made basic with 15 mL of 2.5 N aqueous sodium hydroxide, and extracted with 3×25 mL of ethyl acetate. The ethyl acetate layers were dried over sodium sulfate and evaporated to give 180 mg of the title compound as a colorless syrup. 1NMR (400 MHz, CDCl3): δ 7.26-7.17 (m, 3H), 7.08 (dt, 1H, J=8, 1 Hz), 5.67 (ddt, 1H, J=17, 10, 7 Hz), 4.99 (dq, 1H, J=17, 1 Hz), 4.96 (dm, 1H, J=10 Hz), 2.90-2.80 (m, 2H), 2.78-2.70 (m, 1H), 2.45-2.28 (m, 2H), 2.38 (s, 3H).
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