tert-butyl cyanomethyl carbonate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of potassium cyanide (600 g, 9.22 mol) in methanol (10 L) was added formaldehyde (38% solution in water, 1457 g, 18 mol) dropwise at 0° C. After 1 hour, di-tert-butyl dicarbonate (3018 g, 13.83 mol) was added batchwise at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 4 hours, the reaction mixture was quenched with water (2 L) and extracted with ethyl acetate (4×2 L). The organics were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford tert-butyl cyanomethyl carbonate. The product was used without further purification. After 4 hours the reaction mixture was quenched with water (2 L) extracted with ethyl acetate (4×2 L) dried over sodium sulfate filtered concentrated under reduced pressure