tert-butyl 4-hydroxy-2-Methylpiperidine-1-carboxylate

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

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

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of tert-butyl 2-methyl-4-oxopiperidine-1-carboxylate (727 mg, 3.41 mmol, Small Molecules Inc.) in MeOH (6.0 mL) at 0° C. was added sodium borohydride (193 mg, 5.11 mmol, Aldrich) in several portions. The reaction mixture was stirred at 0° C. for 1 hr and warmed up to room temperature and continuously stirred for another 2.5 hrs. The resulting mixture was then quenched with saturated NH4Cl aqueous solution and evaporated under reduced pressure to remove MeOH followed by extraction with CH2Cl2 (3×). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the title compound (745 mg) as a colorless sticky oil which was used without further purification. warmed up to room temperature continuously stirred for another 2.5 hrs The resulting mixture was then quenched with saturated NH4Cl aqueous solution evaporated under reduced pressure to remove MeOH followed by extraction with CH2Cl2 (3×) The combined extracts were dried (Na2SO4) concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of tert-butyl 2-methyl-4-oxopiperidine-1-carboxylate (727 mg, 3.41 mmol, Small Molecules Inc.) in MeOH (6.0 mL) at 0° C. was added sodium borohydride (193 mg, 5.11 mmol, Aldrich) in several portions. The reaction mixture was stirred at 0° C. for 1 hr and warmed up to room temperature and continuously stirred for another 2.5 hrs. The resulting mixture was then quenched with saturated NH4Cl aqueous solution and evaporated under reduced pressure to remove MeOH followed by extraction with CH2Cl2 (3×). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the title compound (745 mg) as a colorless sticky oil which was used without further purification. warmed up to room temperature continuously stirred for another 2.5 hrs The resulting mixture was then quenched with saturated NH4Cl aqueous solution evaporated under reduced pressure to remove MeOH followed by extraction with CH2Cl2 (3×) The combined extracts were dried (Na2SO4) concentrated in vacuo

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: The title compound was synthesized from tert-butyl 4-hydroxy-2-methylpiperidine-1-carboxylate and 1-(4-((2H-1,2,3-triazol-4-yl)methoxy)-3-fluorophenyl)-1H-tetrazole (Intermediate 16) in a manner similar to that described in Example 48, Step 4. The title compound was isolated as a mixture of four stereoisomers.

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

Procedure: To a solution of tert-butyl 2-methyl-4-oxopiperidine-1-carboxylate (0.94 g, 4.41 mmol) in methanol (5 mL) was added sodium borohydride (0.22 g, 5.73 mmol) and the reaction was stirred at room temperature for 1 h. Water was added slowly, followed by ethyl acetate. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo to afford the desired product as a mixture of four stereoisomers, which was used in the next step without further purification. The layers were separated the aqueous phase was extracted with ethyl acetate The combined organic phases were dried over sodium sulfate filtered concentrated in vacuo

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

Procedure: The title compound was synthesized from tert-butyl 4-hydroxy-2-methylpiperidine-1-carboxylate and 1-(4-((2H-1,2,3-triazol-4-yl)methoxy)-3-fluorophenyl)-1H-tetrazole (Intermediate 16) in a manner similar to that described in Example 48, Step 4. The title compound was isolated as a mixture of four stereoisomers.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of tert-butyl 2-methyl-4-oxopiperidine-1-carboxylate (727 mg, 3.41 mmol, Small Molecules Inc.) in MeOH (6.0 mL) at 0° C. was added sodium borohydride (193 mg, 5.11 mmol, Aldrich) in several portions. The reaction mixture was stirred at 0° C. for 1 hr and warmed up to room temperature and continuously stirred for another 2.5 hrs. The resulting mixture was then quenched with saturated NH4Cl aqueous solution and evaporated under reduced pressure to remove MeOH followed by extraction with CH2Cl2 (3×). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the title compound (745 mg) as a colorless sticky oil which was used without further purification. warmed up to room temperature continuously stirred for another 2.5 hrs The resulting mixture was then quenched with saturated NH4Cl aqueous solution evaporated under reduced pressure to remove MeOH followed by extraction with CH2Cl2 (3×) The combined extracts were dried (Na2SO4) concentrated in vacuo

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