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

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

Procedure: To a solution of the compound prepared in Example 256 (0.123 g) in tetrahydrofuran (1.5 mL) was added sodium hydride (0.057 g) and iodomethane (0.089 mL) at room temperature. The mixture was stirred at room temperature overnight and then diluted with water and ethyl acetate. The organic layer was dried, evaporated in vacuo and purified by column chromatography on silica gel (5% methanol in dichloromethane) to obtain the title compound (0.071 g) having the following physical data. The organic layer was dried evaporated in vacuo purified by column chromatography on silica gel (5% methanol in dichloromethane)

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

Procedure: To a solution of the compound prepared in Example 256 (0.123 g) in tetrahydrofuran (1.5 mL) was added sodium hydride (0.057 g) and iodomethane (0.089 mL) at room temperature. The mixture was stirred at room temperature overnight and then diluted with water and ethyl acetate. The organic layer was dried, evaporated in vacuo and purified by column chromatography on silica gel (5% methanol in dichloromethane) to obtain the title compound (0.071 g) having the following physical data. The organic layer was dried evaporated in vacuo purified by column chromatography on silica gel (5% methanol in dichloromethane)

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

Procedure: To a solution of the compound prepared in Example 256 (0.123 g) in tetrahydrofuran (1.5 mL) was added sodium hydride (0.057 g) and iodomethane (0.089 mL) at room temperature. The mixture was stirred at room temperature overnight and then diluted with water and ethyl acetate. The organic layer was dried, evaporated in vacuo and purified by column chromatography on silica gel (5% methanol in dichloromethane) to obtain the title compound (0.071 g) having the following physical data. The organic layer was dried evaporated in vacuo purified by column chromatography on silica gel (5% methanol in dichloromethane)

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

Procedure: To a solution of the compound prepared in Example 255 (0.500 g) in dioxane (31 mL) and water (3 mL) was treated with sodium azide (0.143 g) at room temperature. The mixture was refluxed overnight. The solvent was evaporated in vacuo and the residue was distributed between ethyl acetate and water. The aqueous layer was extracted with more ethyl acetate, dried and evaporated in vacuo to obtain the title compound (0.534 g) having the following physical data. The mixture was refluxed overnight The solvent was evaporated in vacuo The aqueous layer was extracted with more ethyl acetate dried evaporated in vacuo