Aluminium lithium hydride → 4-chloro-N-(cis-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A 1.0 M solution of lithium aluminum hydride in tetrahydrofuran (7.5 mL, 7.5 mmol) was added dropwise to a solution of cis-methyl 2-(4-chlorophenylsulfonamido)cycloheptanecarboxylate (1.73 g, 5.0 mmol) in 60 mL anhydrous tetrahydrofuran under nitrogen cooled to −60° C. The reaction was stirred for 1.5 h at room temperature and quenched by the slow addition of 150 mL ethyl acetate followed by 150 mL saturated aqueous ammonium chloride. The layers were separated and the aqueous layer was extracted an additional two times with 150 mL ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to yield 4-chloro-N-(cis-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (1.55 g, 98%). 1H NMR (400 MHz, CDCl3) δ ppm 7.82-7.84 (1H, m), 7.80-7.82 (1H, m), 7.48-7.50 (1H, m), 7.45-7.47 (1H, m), 5.13 (1H, d, J=9.57 Hz), 3.70-3.80 (1H, m), 3.61 (1H, dd, J=11.21, 10.20 Hz), 3.41 (1H, dd, J=11.46, 4.66 Hz), 2.69 (1H, br. s.), 1.67-1.83 (1H, m), 1.53-1.62 (2H, m), 1.26-1.51 (7H, m), 1.05-1.20 (1H, m).

Provenance & Evidence