(S)-(+)-2-(Methoxymethyl)pyrrolidine → HCID 11668424, compound

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Reaction Steps

To a solution of 7-chloro-10-oxo-2,3,4,10-tetrahydropyrimido[1,2-a]indole-8-sulfonyl chloride (0.140 g, 0.439 mmol) in CH2Cl2 (10 mL) was added (S)-(+)-2-(methoxymethyl)pyrrolidine (0.119 g, 0.965 mmol, 2.2 eq) drop-wise with cooling in an ice bath under a dry N2 atmosphere. After stirring at room temperature for 1.5 hr, the mixture was quenched with H2O (10 mL) and extracted with EtOAc (3×). The combined organic extracts were dried over MgSO4, filtered, and concentrated to give a film on glass. The film was combined with the product of an earlier run and purified on Biotage KP silica gel eluting with a step gradient of 20/80 petroleum ether/EtOAc, followed by 100% EtOAc to give the title compound as a bright yellow solid (0.104 g, 52.3% yield). Anal. Calc'd. for C17H20ClN3O4S.0.2H2O: C, 50.86; H, 5.12; N, 10.47. Found, C, 50.82; H, 5.00; N, 10.31. NMR (400 MHz, DMSO-d6): consistent. MS: (ES−) m/z 396/398 [M−H] 1 chlorine pattern observed. m.p.: 127-130° C. HRMS: consistent ESI Adduct [M+H] Exact 398.09358, Expt'l 398.09411, mmu 0.53, ppm 1.34, RI % 100.

Provenance & Evidence