Dimethylformamide → HCID 10570280, compound

Participants

Reaction Steps

To a solution of N,N-dimethylformamide (2.54 ml, 35.8 mmol) and methylene chloride (34.5 ml) was added oxalyl chloride (1.53 ml, 17.5 mmol) at -78° C., and the mixture was stirred for 15 min at the same temperature. To the mixture was added dropwise a solution of (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-hydroxymetylpyrrolidine (3.92 g, 11.8 mmol) in methylene chloride (34.5 ml) over a 10 min period. After stirring for 30 min, triethylamine (8.27 ml, 59.3 mmol) was added to the mixture, and the mixture was allowed to warm to room temperature. After stirring for 15 min, the reaction mixture was washed with water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give an oily residue, which was dissolved in benzene (20 ml). To the solution was added trimethylsilylcyanide (1.75 ml, 13.1 mmol), and the mixture was stirred for 12 h at room temperature. To the mixture was added methanol (15 ml), and further stirred. The solvent was removed in vacuo. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=5:1) to give (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(1-cyano-1-hydroxymethyl)pyrrolidine (3.8 g, yield: 88.1%).

Provenance & Evidence