Hydroxylamine → HCID 58374197, compound

Participants

Reaction Steps

(S)-Ethyl-1-((S)-2-(tert-butyldimethylsilyloxy)-2-(4-cyanophenyl)ethyl)piperidine-3-carboxylate (31.0 g, 74.4 mmol) was dissolved in EtOH (248 mL). Hydroxylamine (50% aq) (6.84 ml, 112 mmol) was added and stirred at room temperature overnight. Then all volatiles were removed with ROTAVAPOR®. The residue was purified with on a silica gel cartridge (330 g silica, 0-50% EtOAc/hexanes gradient) to give (S)-ethyl 1-((S)-2-(tert-butyldimethylsilyloxy)-2-(4-((Z)-N′-hydroxycarbamimidoyl)phenyl)ethyl)piperidine-3-carboxylate (31 g, 68.9 mmol, 93% yield) as a white foam. 1H NMR (400 MHz, CDCl3) δ ppm 8.38 (1H, br s), 7.58 (2H, d), 7.37 (2H, d), 4.88 (2H, br s), 4.81 (1H, m), 4.13 (2H, m), 2.96 (1H, m), 2.82 (1H, m), 2.61 (1H, dd), 2.51 (1H, m), 2.42 (1H, dd), 2.32 (1H, tt), 2.13 (1H, dt), 1.91 (1H, m), 1.66 (1H, dt), 1.58 (1H, m), 1.48 (1H, m), 1.27 (3H, t), 0.89 (9H, s), 0.08 (3H, s), −0.09 (3H, s).

Provenance & Evidence