Sodium hydride → HCID 20820309, compound

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Reaction Steps

3.3 g of perhydro-1,5-diazocine-2,6-dione are suspended in 30 ml of absolute DMF, and 732 mg of sodium hydride (80%) are then added. The mixture is stirred at RT for 15 min and then cooled to 0° C., and 3.76 ml of tert-butyl bromoacetate are then added. The mixture is stirred at 0° C. for 15 min and at RT for 30 min and then once more cooled to 0° C., and another 732 mg of sodium hydride (80%) are added. After 15 min, a further 3.76 ml of tert-butyl bromoacetate are added using a pipette, and after 15 min, the ice bath is removed and the mixture is stirred at RT overnight. The mixture is diluted with dichloromethane, water is added, the phases are separated and the organic phase is washed twice with water. The organic phase is dried over MgSO4 and concentrated, and the residue is dried under high vacuum and recrystallized from n-hexane. This gives 2.5 g of the title compound of melting point 180° C.; the mass spectrum shows the molecular peaks MH+ and MNH4+ at 371 and 388 Da, respectively.

Provenance & Evidence