Sodium Cyanide → cis-5-Methoxymethyl-3-Cyano-Cbz-Pyrrolidine

Participants

Reaction Conditions

Reaction Steps

trans-5-Methoxymethyl-3-tosyl-Cbz-pyrrolidine (3.55 g, 8.8 mmol) was dissolved in DMSO (8.8 mL). Finely ground NaCN(0.65 g, 13.2 mmol) was added, and the resulting reaction mixture was stirred 4 h at 80° C. The solution was cooled to room temperature, diluted with H20 (9 mL) and brine (9 mL), and extracted with ethyl acetate. The organic extracts were dried over MgSO4 and concentrated. The crude product was purified by column chromatography eluting with hexanes/ethyl acetate (2/1, v/v) to afford 2.09 g (87% yield) of the desired product as an oil.

Provenance & Evidence