4-Toluenesulfonyl chloride → HCID 58932564, compound

Participants

Reaction Steps

A solution of {(2S)-1-[(3′,3′-dimethyl-3′,4′-dihydro-2′H-spiro[1,3-dioxane-2,10′-pyrimido[1,2-a]indol]-8′-yl)sulfonyl]pyrrolidin-2-yl}methanol (0.100 g, 2.300 mmol), p-toluenesulfonyl chloride (0.070 g, 0.340 mmol), N,N-diisopropylethylamine (0.100 ml, 0.580 mmol) and 4-(dimethylamino)pyridine (0.020 g, 0.070 mmol) in CH2Cl2 (5 mL) was stirred at rt for 2 days. The reaction was poured into brine and extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated to give the title compound as a white foam (0.132 g, 97% ). Anal: Calc'd for C28H35N3O7S2: C, 57.03; H, 5.98; N, 7.13. Found: C, 56.38; H, 5.65; N, 6.81. NMR (400 Mz, DMSO-d6): consistent. MS: (ESI+) m/z 590.3 [M+H].

Provenance & Evidence