1,4-dioxaspiro[4.4]nonane

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of cyclopentanone ethylene ketal (12.82 g, 100 mmol) and ZnI2 (45 mg, catalytic) was placed in water bath and to this was added trimethylsilyl cyanide (13.35 mL, 100 mmol) via syringe over 10 min. After 16 h, EtOH (100 mL) followed by 50% aqueous hydroxylamine (6.43 mL, 100 mmol) was added and stirred at 80° C. for 2 h. Then, the reaction mixture was cooled in ice-water bath and diethyl acetylenedicarboxylate (16 mL, 100 mmol) was added over 5 min. The cooling bath was removed and the reaction stirred for 4 h at room temperature then concentrated to give the title compound as a dark-brown oil LRMS (M+H) calcd for C16H27N2O7: 359.2; found: 359.2. was added The cooling bath was removed the reaction stirred for 4 h at room temperature then concentrated