1-azido-2-[2-(2-azidoethoxy)ethoxy]ethane

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

Procedure: The diazide (17) (3.55 g, 17.85 mmol) in THF (10mL) was added dropwise into a cold (-5° C.) stirred mixture of lithium aluminum hydride (1.83 g, 48.2 mmol) in THF (20 mL). The reaction mixture was kept at -5° C. and carefully quenched with water (10 mL). The THF layer was filtered to remove the inorganic salts, dried over Na2SO4, and evaporated in vacuo to afford the diamine (18) (2.56 g, 97% yield). was kept at -5° C. carefully quenched with water (10 mL) The THF layer was filtered to remove the inorganic salts dried over Na2SO4 evaporated in vacuo

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

Procedure: The diazide (17) (3.55 g, 17.85 mmol) in THF (10mL) was added dropwise into a cold (-5° C.) stirred mixture of lithium aluminum hydride (1.83 g, 48.2 mmol) in THF (20 mL). The reaction mixture was kept at -5° C. and carefully quenched with water (10 mL). The THF layer was filtered to remove the inorganic salts, dried over Na2SO4, and evaporated in vacuo to afford the diamine (18) (2.56 g, 97% yield). was kept at -5° C. carefully quenched with water (10 mL) The THF layer was filtered to remove the inorganic salts dried over Na2SO4 evaporated in vacuo

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

Procedure: To a solution of diazide 19 (14.67 g, 0.073 mol) in THF (100 ml) 1.5 g of 5% Pt on charcoal is added. The mixture is stirred for 12 h under hydrogen. Filtration through Celite™ and evaporation of solvents at reduced pressure gives 1,8-diamino-3,6-dioxa-octane 20. Filtration through Celite™ and evaporation of solvents at reduced pressure

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

Procedure: To a solution of diazide 19 (14.67 g, 0.073 mol) in THF (100 ml) 1.5 g of 5% Pt on charcoal is added. The mixture is stirred for 12 h under hydrogen. Filtration through Celite™ and evaporation of solvents at reduced pressure gives 1,8-diamino-3,6-dioxa-octane 20. Filtration through Celite™ and evaporation of solvents at reduced pressure

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

Procedure: The diazide (17) (3.55 g, 17.85 mmol) in THF (10 mL) was added dropwise into a cold (-5° C.) stirred mixture of lithium aluminum hydride (1.83 g, 48.2 mmol) in THF (20 mL). The reaction mixture was kept at -5° C. and carefully quenched with water (10 mL). The THF layer was filtered to remove the inorganic salts, dried over Na2SO4, and evaporated in vacuo to afford the diamine (18) (2.56 g, 97% yield). was kept at -5° C. carefully quenched with water (10 mL) The THF layer was filtered to remove the inorganic salts dried over Na2SO4 evaporated in vacuo

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

Procedure: The diazide (17) (3.55 g, 17.85 mmol) in THF (10mL) was added dropwise into a cold (-5° C.) stirred mixture of lithium aluminum hydride (1.83 g, 48.2 mmol) in THF (20 mL). The reaction mixture was kept at -5° C. and carefully quenched with water (10 mL). The THF layer was filtered to remove the inorganic salts, dried over Na2SO4, and evaporated in vacuo to afford the diamine (18) (2.56 g, 97% yield). was kept at -5° C. carefully quenched with water (10 mL) The THF layer was filtered to remove the inorganic salts dried over Na2SO4 evaporated in vacuo