7-azidoheptan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: TsCl (955 mg, 5.0 mmol) and pyridine (435 μL, 5.4 mmol) were added to a solution of 7-azidoheptanol (700 mg, 4.5 mmol) in CH2Cl2 (5 mL). The solution was stirred for 18 h at r.t. The solution was diluted with EtOAc (20 mL) and washed with 5% aqueous KHSO4 solution, sat. aqueous NaHCO3 solution and pH 7 phosphate buffer. The org. layer was concentrated and the residue was treated with water (10 mL) for 4 h to hydrolyse excess TsCl. The mixture was diluted with EtOAc (20 mL), washed with aqueous NaHCO3, dried (Na2SO4), and filtered. Concentration under reduced pressure yielded 7-azidoheptyltosylate (920 mg, 66%). The product was pure enough for further reactions. washed with 5% aqueous KHSO4 solution, sat. aqueous NaHCO3 solution and pH 7 phosphate buffer layer was concentrated the residue was treated with water (10 mL) for 4 h to hydrolyse excess TsCl The mixture was diluted with EtOAc (20 mL) washed with aqueous NaHCO3 dried (Na2SO4) filtered Concentration under reduced pressure

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

Procedure: NaN3 (390 mg, 6.0 mmol) was added to a solution of 7-bromoheptanol (880 μL, 5.7 mmol) in DMF (5 mL). The mixture was stirred for 24 at r.t. and additional 3 h at 80° C. to complete the reaction. The mixture was concentrated under reduced pressure, the residue was dissolved in water/Et2O (10/20 mL), the organic layer was separated, dried over Na2SO4 and filtered. Concentration under reduced pressure yielded 7-azidoheptanol (710 mg, 78%) as an colourless oil which was pure enough for further reactions. the reaction The mixture was concentrated under reduced pressure the residue was dissolved in water/Et2O (10/20 mL) the organic layer was separated dried over Na2SO4 filtered Concentration under reduced pressure