Water → 3-(5'-Chloro-2'-oxospiro[1,3-dioxane-2,3'-indol]-1'(2'H)-yl)-2,2-dimethylpropanenitrile

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Reaction Conditions

Reaction Steps

To a stirred solution of potassium t-butoxide (0.561 g, 5.00 mmol, 1.2 eq) in anhydrous DMSO (16 mL) was added 5′-chlorospiro[1,3-dioxane-2,3′-indol]-2′(1′H)-one (1.00 g, 4.17 mmol) all in one portion. After stirring 10 min. 3-chloro-2,2-dimethylpropionitrile (0.981 g, 8.34 mmol, 2 eq) was added in one portion at room temperature under a dry N2 atmosphere. The reaction was heated at 125° C. for 22 hr, cooled to room temperature, poured into H2O (180 mL) and extracted with Et2O (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated. The crude product was purified on Biotage KP silica gel eluting with 100% CH2Cl2 to give the title compound as a white solid (0.91 g, 68% yield). Anal. Calc'd for C16H17ClN2O3: C, 59.91; H, 5.34; N, 8.73. Found: C, 59.79; H, 5.26; N, 8.57. NMR (300 Mz, DMSO-d6): consistent. IR: consistent. MS: (ES+) m/z 321 [M+H]; one Cl pattern observed. m.p.: 114-115.5° C.

Provenance & Evidence