C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2=[C:9]([CH:23]=1)[O:10][CH2:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1/[C:14]/2=[C:15](/[C:17]#[N:18])\[CH3:16])=O.[BH4-].[Li+].Cl>C1COCC1>[OH:2][CH2:3][C:5]1[CH:6]=[CH:7][C:8]2=[C:9]([CH:23]=1)[O:10][CH2:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1/[C:14]/2=[C:15](\[CH3:16])/[C:17]#[N:18][step 2] (Z)-11-(1-Cyanoethylidene)-6,11-dihydrodibenzo[b,e]oxepine-3-carboxylic acid methyl ester (0.557 g, 1.82 mmol) was suspended in THF (9 mL), lithium borohydride (0.199 g, 9.12 mmol) was added and the mixture was stirred at 50° C. for 8 hr. To the mixture was added ice, and the mixture was neutralized to pH 2 with 1 mol/L hydrochloric acid, and extracted twice with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Isopropyl alcohol (13 mL) was added to the residue, and the mixture was filtered to give the title compound (0.364 g, 72%).
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