1-(Chloromethyl)cycloheptane-1-carbonitrile → 8'-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]sulfonyl}spiro[cycloheptane-1,3'-pyrimido[1,2-a]indol]-10'(2'H)-one

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Reaction Steps

The title compound was prepared as a yellow foam from 5′-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]sulfonyl}spiro[1,3-dioxolane-2,3′-indol]-2′(1′H)-one and 1-chloromethyl-cycloheptanecarbonitrile (Syn. Comm. 20(12) 1757, 1990) using a procedure similar to that of steps 3-5 of Example 12. The crude product was purified on Biotage KP silica gel eluting with CH2Cl2/EtOAc (9:1). NMR (400 Mz, DMSO-d6): consistent. Analytical HPLC (Chromolith Monolith 0.46×10 cm column, gradient of acetonitrile in water/trifluoroacetic acid): 93.2% (254 nm). MS: (API-ES+) m/z 446.2 [M+H]; (API-ES−) m/z 444.2 [M−H].

Provenance & Evidence