[CH3:1][CH:2]1[C:8](=O)[CH2:7][CH:6]2[N:10]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=3)[CH:3]1[CH2:4][CH2:5]2.C1(C)C=CC(S(NN)(=O)=O)=CC=1.C([BH3-])#N.[Na+].S1(CCCC1)(=O)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C.O.C1CCCCC1.CN(C)C=O>[CH3:1][CH:2]1[CH2:8][CH2:7][CH:6]2[N:10]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=3)[CH:3]1[CH2:4][CH2:5]2159JP84 (115 mg, 0.40 mmol) and p-toluenesulfonhydrazide (90 mg, 0.48 mmol) in absolute ethanol (1.0 mL) were refluxed overnight and the resulting white precipitate was filtered off, dried in vacuo and added to a vial containing sodium cyanoborohydride (101 mg, 1.60 mmol), N,N-dimethylformamide (2.0 mL), sulfolane (2.0 mL), p-toluenesulfonic acid (25 mg) and cyclohexane (2.0 mL). The resulting solution was heated at 110° C. for 2 days, poured into water (200 mL), extracted with ethyl acetate (2×200 mL), dried over Na2SO4, filtered, concentrated in vacuo and purified by preparative TLC (ethyl acetate/n-heptane 1:5, 5× eluted) to afford the title compound (25.3 mg, 22%) as thick oil.
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