Pentanal → 4-Chloro-6-methyl-10,10-dioxo-2-(4-pentyl-piperazin-1-yl)-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

Pentanaldehyde (0.042 gm, 0.5 mmol) was added with stirring to a solution of Example 104k (0.180 g, 0.4 mmol) in dry methanol (10 mL). Titanium isopropoxide (0.117 g, 0.4 mmol) was added and the reaction mixture was cooled to 10° C. Sodium cyanoborohydride (51 mg, 0.8 mmol) was added and the reaction mixture was heated at 60° C. overnight. It was concentrated, treated with water and extracted with n-butanol. The organic layer was washed with water, brine, concentrated and purified using flash chromatography (silica gel, 1-3% MeOH/CHCl3) to obtain the title compound. Yield: 0.2 g (99%), 1H NMR (CDCl3): δ 0.90 (s, 3H, CH3), 1.3 (t, 4H, 2CH2), 1.7 (t, 2H, CH2), 2.40 (t, 2H, CH2), 2.8 (t, 4H, 2CH2), 2.90 (s, 3H, CH3), 3.20 (t, 4H, 2CH2), 3.90 (s, 3H, CH3), 4.8 (s, 2H, CH2), 6.70 (s, 1H, Ar), 6.90 (s, 1H, Ar). 8.1 (s 1H Ar), 8.4 (s 1H Ar); MS: m/e (EI+) 507 (M+1).

Provenance & Evidence