Water → 4-Chloro-6-methyl-2-[4-(2-methyl-benzyl)-piperazin-1-yl]-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

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Reaction Conditions

Reaction Steps

o-Tolualdehyde (0.041 mL, 0.35 mmol) and titanium isopropoxide (0.136 mL, 0.45 mmol) were added to a suspension of Example 104k (0.16 g, 0.36 mmol) in methanol (7 mL). The reaction mixture was stirred at 70° C. for 1.5 h, cooled to room temperature, treated with sodium cyanoborohydride (0.022 g, 0.34 mmol), then stirred at 70° C. for 1 h and at room temperature overnight. It was treated with water and extracted with n-butanol. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, ethyl acetate/pet ether) to obtain the title compound. Yield: 0.060 g, (30%); 1H NMR (CDCl3): δ 2.4 (s, 3H, CH3), 2.6 (t, 4H, 2CH2), 2.71 (s, 3H, CH3), 3.21 (t, 4H, 2CH2), 3.53 (s, 2H, CH2), 3.92 (s, 3H, OCH3), 4.67 (s, 2H, CH2), 6.74 (d, 1H, Ar), 6.88 (d, 1H, Ar), 7.13 (t, 1H, Ar), 8.07 (d, 1H, Ar), 8.43 (d, 1H, Ar); MS: m/e (ES+) 542 (M+1).

Provenance & Evidence