反应详情

A solution of trans-methyl 2-aminocycloheptanecarboxylate acetate (652 mg, 2.82 mmol), 4-chlorobenzene sulfonyl chloride (893 mg, 4.23 mmol), and triethylamine (1.18 mL, 8.46 mmol) was stirred in 20 mL tetrahydrofuran for 2 h. The reaction was partitioned between 100 mL diethyl ether and 100 mL brine. The organic layer was dried over sodium sulfate, concentrated, and purified by flash chromatography on 40 g silica gel with 15 to 40% ethyl acetate in hexane to yield trans-methyl 2-(4-chlorophenylsulfonamido)cycloheptanecarboxylate (253 mg, 26%). 1H NMR (400 MHz, CDCl3) δ ppm 7.77-7.79 (1H, m), 7.74-7.76 (1H, m), 7.44-7.47 (1H, m), 7.42-7.44 (1H, m), 5.21 (1H, d, J=8.56 Hz), 3.68 (1H, qd, J=8.48, 3.78 Hz), 3.43 (3H, s), 2.44 (1H, td, J=8.56, 3.27 Hz), 1.75-1.82 (1H, m), 1.56-1.73 (4H, m), 1.34-1.54 (5H, m). LC/MS R.T.=2.89 min; [M−H]+=344.04; [M+Na]+=368.16; [M−H]−=344.04.

1. customThe reaction was partitioned between 100 mL diethyl ether and 100 mL brine
2. dry with materialThe organic layer was dried over sodium sulfate
3. concentrationconcentrated
4. custompurified by flash chromatography on 40 g silica gel with 15 to 40% ethyl acetate in hexane