methyl 1-benzyl-4-hydroxypiperidine-4-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:0.00; pressure:0.00; stir:

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 1-benzyl-4-hydroxy-4-piperidinecarboxylate (15.0 g, 77 mmol), 2,3-dichloropyridine (12.0 g, 81 mmol), and potassium carbonate (15.0 g, 108.7 mmol) were combined in DMF (200 mL) and heated at 90° C. for 2 days. The mixture was allowed to cool to room temperature, concentrated, and standard work-up provided a residue that was purified via chromatography (SiO2, ethyl acetate:hexanes, 1:6) to provide the title compound MS (EI, M+H)+ 271. to cool to room temperature concentrated standard work-up provided a residue that was purified via chromatography (SiO2, ethyl acetate:hexanes, 1:6)

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

Procedure: Methyl 1-benzyl-4-hydroxy-4-piperidinecarboxylate in methanol was treated with Pd(OH)2 (20% on carbon, 500 mg) under a hydrogen atmosphere. The mixture was allowed to stir at room temperature for 12 hours, filtered, and the filtrate was concentrated under reduced pressure. filtered the filtrate was concentrated under reduced pressure

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

Procedure: 1-Benzyl-4-hydroxy-4-piperidinecarbonitrile (30.0 g, 118 mmol) in methanol (590 mL) and concentrated HCl (590 mL) was heated at reflux for 18 hours. The product was obtained following chromatography (SiO2, ethyl acetate:hexane, 1:4). MS (EI, M+H)+ 250. at reflux for 18 hours The product was obtained

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 1-benzyl-4-hydroxy-4-piperidinecarboxylate (15.0 g, 77 mmol), 2,3-dichloropyridine (12.0 g, 81 mmol), and potassium carbonate (15.0 g, 108.7 mmol) were combined in DMF (200 mL) and heated at 90° C. for 2 days. The mixture was allowed to cool to room temperature, concentrated, and standard work-up provided a residue that was purified via chromatography (SiO2, ethyl acetate:hexanes, 1:6) to provide the title compound MS (EI, M+H)+271. to cool to room temperature concentrated standard work-up provided a residue that was purified via chromatography (SiO2, ethyl acetate:hexanes, 1:6)

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

Procedure: Methyl 1-benzyl-4-hydroxy-4-piperidinecarboxylate in methanol was treated with Pd(OH)2 (20% on carbon, 500 mg) under a hydrogen atmosphere. The mixture was allowed to stir at room temperature for 12 hours, filtered, and the filtrate was concentrated under reduced pressure. filtered the filtrate was concentrated under reduced pressure

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

Procedure: 1-Benzyl-4-hydroxy-4-piperidinecarbonitrile (30.0 g, 118 mmol) in methanol (590 mL) and concentrated HCl (590 mL) was heated at reflux for 18 hours. The product was obtained following chromatography (SiO2, ethyl acetate:hexane, 1:4). MS (EI, M+H)+250. at reflux for 18 hours The product was obtained