1,5-Di(4-toluenesulfonamido)-3,7-bismethylenediazacyclooctane → 1,5-Dimethyl-3,7-diazabicyclooctane

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Reaction Steps

In separate experiments a suspension of 1,5-di(4-toluenesulfonamido)-3,7-bismethylenediazacyclooctane 1a (0.223 g, 0.50 mmol) in tetrahydrofuran (50 mL) containing either lithium aluminum hydride (0.25 g, 6.6 mmol) or lithium aluminum deuteride (0.25 g, 6.0 mmol) was stirred under a nitrogen atmosphere for 42 h. The reaction mixture was quenched by the dropwise addition D2O (1 mL) followed by 40% sodium hydroxide or 40% sodium deuteroxide solution (0.5 mL) with external cooling. Stirring was continued at room temperature for 5 h and the white granular precipitate that formed was removed by filtration and washed with anhydrous ether (3×50 mL). The combined organic extracts were concentrated on a rotary evaporator to give 0.052 g 0.057 g (82%) of 5 as a colorless solid, mp XX° C. The crude product was dissolved in benzene (25 mL) to which was added H2O (3×1 mL) and the mixture was subjected to azeotropic distillation using a Dean Stark tube. Analysis of the product by Cl NH3MS showed:

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