4-Toluenesulfonyl chloride → 2'-amino-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-4'-yl 4-methylbenzenesulfonate

Participants

Reaction Steps

A solution of Example 10C (2.91 g, 13.27 mmol), p-toluenesulfonyl chloride (3.79 g, 19.91 mmol), and 4-(dimethylamino)pyridine (324 mg, 2.65 mmol) in methylene chloride (60 mL) was treated with triethylamine (3.7 mL, 4.40 mmol) at ambient temperature, and the resulting solution was stirred for 3 hours. It was then diluted with methylene chloride (100 mL) and water (50 mL), and the layers were separated. The organic layer was dried with magnesium sulfate and concentrated under reduced pressure; then the residue was chromatographed on silica gel (1:2:2 ethyl acetate/methylene chloride/hexane, eluant) to provide the title product. 1H NMR (300 MHz, CD3OD) δ 7.95 (d, 2H), 7.44 (d, 2H), 2.45-2.47 (m, 3H), 2.40-2.45 (m, 2H), 1.99-2.10 (m, 2H), 1.79-1.90 (m, 2H) 1.65-1.75 (m, 6H), 1.52-1.62 (m, 2H); MS (DCI+) m/z 374 (M+H)+.

Provenance & Evidence