Aluminium lithium hydride → HCID 59497810, compound

Participants

Reaction Steps

A 1.0 M solution of lithium aluminum hydride in tetrahydrofuran (1.10 mL, 1.10 mmol) was added dropwise to a solution of trans-methyl 2-(4-chlorophenylsulfonamido)cycloheptanecarboxylate (253 mg, 0.73 mmol) in anhydrous tetrahydrofuran at −60° C. under nitrogen. The reaction was stirred at room temperature for 1.5 h and quenched by the addition of 25 mL ethyl acetate. The reaction was extracted twice with 25 mL saturated aqueous ammonium chloride. The organic layer was dried over sodium sulfate and concentrated to yield 4-chloro-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (216 mg, 93%). 1H NMR (400 MHz, CDCl3) δ ppm 7.81-7.83 (1H, m), 7.79-7.80 (1H, m), 7.47-7.49 (1H, m), 7.44-7.46 (1H, m), 5.40 (1H, d, J=8.06 Hz), 3.64 (1H, dd, J=11.08, 4.78 Hz), 3.48 (1H, dd, J=10.95, 4.41 Hz), 3.15-3.27 (1H, m), 2.27 (1H, br. s.), 1.58-1.72 (2H, m), 1.42-1.55 (5H, m), 1.21-1.39 (4H, m). LC/MS R.T.=2.18 min; [M+H]+=318.08; [M+Na]+=340.09; [M−H]−=316.07.

Provenance & Evidence