tert-butyl-dimethyl-(piperidin-2-ylmethoxy)silane

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

Procedure: To a DMF (4 ml) solution of 60% sodium hydride (0.21 g, 5.2 mmol) was dropwise added a DMF (4 ml) solution of 2-(tert-butyldimethylsilyloxymethyl)piperidine (1.00 g, 4.4 mmol) at room temperature. The mixture was stirred at room temperature for 30 min., to which was then dropwise added a THF (1 ml) solution of benzyl bromide (0.75 g, 4.4 mmol). After stirring at room temperature for additional 30 min., a reaction solution was poured onto water followed by extraction with diethyl ether (30 ml). The extract was washed successively with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 1.30 g of the title compound. After stirring at room temperature for additional 30 min. a reaction solution was poured onto water followed by extraction with diethyl ether (30 ml) The extract was washed successively with water and saturated aqueous sodium chloride dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure

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

Procedure: To a DMF (3 ml) solution of 2-piperidinemethanol (1.00 g, 8.7 mmol) and imidazole (1.48 g, 21.7 mmol) was added tert-butyldimethylchlorosilane (1.57 g, 10.4 mmol) at room temperature. After stirring for 30 min., a reaction solution was poured onto water followed by extraction with diethyl ether (about 30 ml). The extract was washed successively with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to afford 1.61 g of the title compound. a reaction solution was poured onto water followed by extraction with diethyl ether (about 30 ml) The extract was washed successively with water and saturated aqueous sodium chloride dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure

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

Procedure: To a DMF (3 ml) solution of 2-piperidinemethanol (1.00 g, 8.7 mmol) and imidazole (1.48 g, 21.7 mmol) was added tert-butyldimethylchlorosilane (1.57 g, 10.4 mmol) at room temperature. After stirring for 30 min., a reaction solution was poured onto water followed by extraction with diethyl ether (about 30 ml). The extract was washed successively with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to afford 1.61 g of the title compound. a reaction solution was poured onto water followed by extraction with diethyl ether (about 30 ml) The extract was washed successively with water and saturated aqueous sodium chloride dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure

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

Procedure: To a DMF (4 ml) solution of 60% sodium hydride (0.21 g, 5.2 mmol) was dropwise added a DMF (4 ml) solution of 2-(tert-butyldimethylsilyloxymethyl)piperidine (1.00 g, 4.4 mmol) at room temperature. The mixture was stirred at room temperature for 30 min., to which was then dropwise added a THF (1 ml) solution of benzyl bromide (0.75 g, 4.4 mmol). After stirring at room temperature for additional 30 min., a reaction solution was poured onto water followed by extraction with diethyl ether (30 ml). The extract was washed successively with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 1.30 g of the title compound. After stirring at room temperature for additional 30 min. a reaction solution was poured onto water followed by extraction with diethyl ether (30 ml) The extract was washed successively with water and saturated aqueous sodium chloride dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure

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

Procedure: To a DMF (3 ml) solution of 2-piperidinemethanol (1.00 g, 8.7 mmol) and imidazole (1.48 g, 21.7 mmol) was added tert-butyldimethylchlorosilane (1.57 g, 10.4 mmol) at room temperature. After stirring for 30 min., a reaction solution was poured onto water followed by extraction with diethyl ether (about 30 ml). The extract was washed successively with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to afford 1.61 g of the title compound. a reaction solution was poured onto water followed by extraction with diethyl ether (about 30 ml) The extract was washed successively with water and saturated aqueous sodium chloride dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure