tert-butyl 4-(azidomethyl)-4-hydroxypiperidine-1-carboxylate synthesis

Yield:863561-68-6 90%

Reaction Conditions:

with sodium azide;ammonium chloride in methanol;water; for 15 h;Heating / reflux;

Steps:

7

A solution of D7 (3.9g ; 18. 3 mmol) in MeOH (100 ml) and water (20 ml) was treated with sodium azide (5.95 g; 91.5 mmol) and ammonium chloride (1.96 g; 36. 6 mmol). The mixture was heated under reflux for 15 hours. The solvents were removed by evaporation and the residue partitioned between water and CH2C12. The CH2C12 was evaporated and the residue purified by flash chromatography eluting with increasingly polar mixtures of EtOAc/hexanes (20-30% EtOAc) to give E7 (4.24 g). Yield: 90%

References:

WO2005/79805,2005,A1 Location in patent:Page/Page column 73