Sodium Cyanide → HCID 59271815, compound

Participants

Reaction Steps

To a solution of (4S)-5-(benzyloxy)-4-methoxypentanal (109 g, 490 mmol) in dioxane (500 mL) at room temperature was added EtNH2.HCl (60 g, 736 mmol), NaCN (36 g, 736 mmol), and H2O (500 mL). The reaction mixture was stirred for 2 days, then diluted with saturated aqueous NaHCO3 and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. To a solution of the crude residue in EtOAc (500 mL) was added (Boc)2O (107 g, 492 mmol). The resulting mixture was stirred at 40° C. for 2 days. The reaction mixture was cooled to ambient temperature, diluted water, and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. Flash column chromatography eluted with 10 to 40% EtOAc in hexanes provided tert-butyl[(4S)-5-(benzyloxy)-1-cyano-4-methoxypentyl]ethylcarbamate. LC-MS: 377.4 (M+1).

Provenance & Evidence