تفاعل #520503

معادلة التفاعل

N-{2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-3-hydroxybutyl]-1,3-dioxoisoindolin-4-yl}acetamide

pyridinium chlorochromate

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N-{2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-3-oxobutyl]-1,3-di-oxoisoindolin-4-yl}acetamide

المردود 85.6%

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe mixture was filtered through celite
2. 2
   غسيلthe filtrate was washed with water (30 mL), brine (30 mL)
3. 3
   تجفيفdried over magnesium sulfate
4. 4
   أخرىThe solvent was removed in vacuo
5. 5
   أخرىthe residue was purified by chromatography (Silica gel, methylene chloride:ethyl acetate 9:1)

الإجراء التجريبي

A mixture of N-{2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-3-hydroxybutyl]-1,3-dioxoisoindolin-4-yl}acetamide (1.28g, 2.74 mmol), pyridinium chlorochromate (1.18 g, 5.48 mmol) and celite (0.6 g) in methylene chloride (35 mL) was stirred at room temperature for 5 hours. The mixture was filtered through celite and the filtrate was washed with water (30 mL), brine (30 mL) and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was purified by chromatography (Silica gel, methylene chloride:ethyl acetate 9:1) to give N-{2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-3-oxobutyl]-1,3-di-oxoisoindolin-4-yl}acetamide (1.09 g, 85%) as a white solide: mp 145-147° C.; 1H NMR (CDCl3) δ9.53 (s, 1H), 8.70 (d, J=8.4 Hz, 1H), 7.62 (t, J=7.6 Hz, 1H), 7.46 (d, J=7.3 Hz, 1H), 7.07-7.01 (m, 2H), 6.81 (d, J=8.2 Hz, 1H), 5.73-5.67 (dd, J=5.1, 9.8 Hz, 1H), 4.77 (m, 1H), 4.04-3.93 (dd, J=10.0, 18.1 Hz, 1H), 3.80 (s, 3H), 3.28-3.19 (dd, J=5.1, 18.0 Hz, 1H), 2.26 (s, 3H), 2.18 (s, 3H), 1.97-1.61 (m, 8H); 13C NMR (CDCl3) δ205.22, 170.03, 169.15, 167.82, 149.83, 147.70, 137.33, 135.77, 131.23, 124.63, 119.88, 117.87, 115.28, 114.57, 111.72, 80.46, 55.99, 49.94, 44.82, 32.75, 30.14, 24.92, 24.05; Anal. Calcd. for C26H28N2O6; C, 67.23; H, 6.08; N, 6.03. Found: C, 66.96; H, 6.06; N, 5.89.

المصدر