p-Bromobenzenesulfonyl chloride → 4-bromo-N-((1R,2R)-2-methylcyclopropyl)benzenesulfonamide

Temperature

0 °C

A solution of benzyl ((1R,2R)-2-methylcyclopropyl)carbamate (1.68 g, 8.2 mmol) in DCM (55 mL) was charged with 10 wt % Pd/C, then degassed and charged with hydrogen (50 PSI). The reaction was complete after 30 min and so was filtered over celite, rinsing with DCM (15 mL). The liquor was cooled to 0° C., and treated with triethylamine (3.43 mL, 24.6 mmol) and 4-bromobenzene-1-sulfonyl chloride (2.20 g, 8.61 mmol). The cold bath was removed and the reaction was stirred for 1 h. At completion, the reaction was washed with 0.5 M aq. HCl (2×20 mL) and brine (20 mL), dried over MgSO4 and concentrated to provide 4-bromo-N-((1R,2R)-2-methylcyclopropyl)benzenesulfonamide (2.06 g, 87% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.74-7.80 (m, 1H), 7.66-7.72 (m, 1H), 4.90 (br. s., 1H), 1.94 (dt, J=3.5, 1.8 Hz, 1H), 1.41 (t, J=7.3 Hz, 1H), 0.89-1.01 (m, 3H), 0.70-0.81 (m, 1H), 0.35-0.45 (m, 1H).

1. customdegassed
2. additioncharged with hydrogen (50 PSI)
3. filtrationso was filtered over celite
4. washrinsing with DCM (15 mL)
5. customThe cold bath was removed
6. washAt completion, the reaction was washed with 0.5 M aq. HCl (2×20 mL) and brine (20 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated

ORD record

ord-1a7b9b0dc49b42f0b9394e8016714926

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08440652B2