ethyl 9-azabicyclo[3.3.1]nonane-3-carboxylate

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

Procedure: To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet were added 5.59 g (28.36 mmol) ethyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 142 mL ethanol, and 9.47 g (56.72 mmol) ethyl bromoacetate. The reaction was refluxed 3 days, cooled, and evaporated. The residue was partitioned between methylene chloride and aqueous sodium hydroxide, and the organic layer was dried over sodium sulfate and evaporated. The residue was filtered through silica gel using ethyl acetate to afford an oil, 4.835 g (100% yield crude), as a mixture of diastereomers. To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet The reaction was refluxed 3 days cooled evaporated The residue was partitioned between methylene chloride and aqueous sodium hydroxide the organic layer was dried over sodium sulfate evaporated The residue was filtered through silica gel to afford an oil, 4.835 g (100% yield crude) as a mixture of diastereomers

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

Procedure: To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet were added 8.14 g (28.36 mmol) ethyl-N-benzyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 60 mL ethanol, 8.93 g (141.8 mmol) ammonium formate, and 5 g 10% palladium-on-carbon. The reaction was refluxed and fresh catalyst and ammonium formate were added until the starting material disappeared (about 4 hr, a total of 8 g catalyst). The reaction was cooled, filtered through diatomaceous earth (Celite [trademark]), and evaporated. The residue was partitioned between methylene chloride and an aqueous sodium hydroxide solution, and the organic layer separated, dried over sodium sulfate, and evaporated. The resulting oil was used directly in the next step. To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet The reaction was refluxed about 4 hr The reaction was cooled filtered through diatomaceous earth (Celite [trademark]) evaporated The residue was partitioned between methylene chloride an aqueous sodium hydroxide solution, and the organic layer separated dried over sodium sulfate evaporated

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

Procedure: To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet were added 5.59 g (28.36 mmol) ethyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 142 mL ethanol, and 9.47 g (56.72 mmol) ethyl bromoacetate. The reaction was refluxed 3 days, cooled, and evaporated. The residue was partitioned between methylene chloride and aqueous sodium hydroxide, and the organic layer was dried over sodium sulfate and evaporated. The residue was filtered through silica gel using ethyl acetate to afford an oil, 4.835 g (100% yield crude), as a mixture of diastereomers. To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet The reaction was refluxed 3 days cooled evaporated The residue was partitioned between methylene chloride and aqueous sodium hydroxide the organic layer was dried over sodium sulfate evaporated The residue was filtered through silica gel to afford an oil, 4.835 g (100% yield crude) as a mixture of diastereomers

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

Procedure: To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet were added 8.14 g (28.36 mmol) ethyl-N-benzyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 60 mL ethanol, 8.93 g (141.8 mmol) ammonium formate, and 5 g 10% palladium-on-carbon. The reaction was refluxed and fresh catalyst and ammonium formate were added until the starting material disappeared (about 4 hr, a total of 8 g catalyst). The reaction was cooled, filtered through diatomaceous earth (Celite [trademark]), and evaporated. The residue was partitioned between methylene chloride and an aqueous sodium hydroxide solution, and the organic layer separated, dried over sodium sulfate, and evaporated. The resulting oil was used directly in the next step. To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet The reaction was refluxed about 4 hr The reaction was cooled filtered through diatomaceous earth (Celite [trademark]) evaporated The residue was partitioned between methylene chloride an aqueous sodium hydroxide solution, and the organic layer separated dried over sodium sulfate evaporated

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

Procedure: To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet were added 8.14 g (28.36 mmol) ethyl-N-benzyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 60 mL ethanol, 8.93 g (141.8 mmol) ammonium formate, and 5 g 10% palladium-on-carbon. The reaction was refluxed and fresh catalyst and ammonium formate were added until the starting material disappeared (about 4 hr, a total of 8 g catalyst). The reaction was cooled, filtered through diatomaceous earth (Celite [trademark]), and evaporated. The residue was partitioned between methylene chloride and an aqueous sodium hydroxide solution, and the organic layer separated, dried over sodium sulfate, and evaporated. The resulting oil was used directly in the next step. To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet The reaction was refluxed about 4 hr The reaction was cooled filtered through diatomaceous earth (Celite [trademark]) evaporated The residue was partitioned between methylene chloride an aqueous sodium hydroxide solution, and the organic layer separated dried over sodium sulfate evaporated

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

Procedure: To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet were added 5.59 g (28.36 mmol) ethyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 142 mL ethanol, and 9.47 g (56.72 mmol) ethyl bromoacetate. The reaction was refluxed 3 days, cooled, and evaporated. The residue was partitioned between methylene chloride and aqueous sodium hydroxide, and the organic layer was dried over sodium sulfate and evaporated. The residue was filtered through silica gel using ethyl acetate to afford an oil, 4.835 g (100% yield crude), as a mixture of diastereomers. To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet The reaction was refluxed 3 days cooled evaporated The residue was partitioned between methylene chloride and aqueous sodium hydroxide the organic layer was dried over sodium sulfate evaporated The residue was filtered through silica gel to afford an oil, 4.835 g (100% yield crude) as a mixture of diastereomers

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

Procedure: To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet were added 8.14 g (28.36 mmol) ethyl-N-benzyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 60 mL ethanol, 8.93 g (141.8 mmol) ammonium formate, and 5 g 10% palladium-on-carbon. The reaction was refluxed and fresh catalyst and ammonium formate were added until the starting material disappeared (about 4 hr, a total of 8 g catalyst). The reaction was cooled, filtered through diatomaceous earth (Celite [trademark]), and evaporated. The residue was partitioned between methylene chloride and an aqueous sodium hydroxide solution, and the organic layer separated, dried over sodium sulfate, and evaporated. The resulting oil was used directly in the next step. To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet The reaction was refluxed about 4 hr The reaction was cooled filtered through diatomaceous earth (Celite [trademark]) evaporated The residue was partitioned between methylene chloride an aqueous sodium hydroxide solution, and the organic layer separated dried over sodium sulfate evaporated

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

Procedure: To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet were added 5.59 g (28.36 mmol) ethyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 142 mL ethanol, and 9.47 g (56.72 mmol) ethyl bromoacetate. The reaction was refluxed 3 days, cooled, and evaporated. The residue was partitioned between methylene chloride and aqueous sodium hydroxide, and the organic layer was dried over sodium sulfate and evaporated. The residue was filtered through silica gel using ethyl acetate to afford an oil, 4.835 g (100% yield crude), as a mixture of diastereomers. To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet The reaction was refluxed 3 days cooled evaporated The residue was partitioned between methylene chloride and aqueous sodium hydroxide the organic layer was dried over sodium sulfate evaporated The residue was filtered through silica gel to afford an oil, 4.835 g (100% yield crude) as a mixture of diastereomers

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

Procedure: To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet were added 8.14 g (28.36 mmol) ethyl-N-benzyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 60 mL ethanol, 8.93 g (141.8 mmol) ammonium formate, and 5 g 10% palladium-on-carbon. The reaction was refluxed and fresh catalyst and ammonium formate were added until the starting material disappeared (about 4 hr, a total of 8 g catalyst). The reaction was cooled, filtered through diatomaceous earth (Celite [trademark]), and evaporated. The residue was partitioned between methylene chloride and an aqueous sodium hydroxide solution, and the organic layer separated, dried over sodium sulfate, and evaporated. The resulting oil was used directly in the next step. To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet The reaction was refluxed about 4 hr The reaction was cooled filtered through diatomaceous earth (Celite [trademark]) evaporated The residue was partitioned between methylene chloride an aqueous sodium hydroxide solution, and the organic layer separated dried over sodium sulfate evaporated

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

Procedure: To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet were added 5.59 g (28.36 mmol) ethyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 142 mL ethanol, and 9.47 g (56.72 mmol) ethyl bromoacetate. The reaction was refluxed 3 days, cooled, and evaporated. The residue was partitioned between methylene chloride and aqueous sodium hydroxide, and the organic layer was dried over sodium sulfate and evaporated. The residue was filtered through silica gel using ethyl acetate to afford an oil, 4.835 g (100% yield crude), as a mixture of diastereomers. To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet The reaction was refluxed 3 days cooled evaporated The residue was partitioned between methylene chloride and aqueous sodium hydroxide the organic layer was dried over sodium sulfate evaporated The residue was filtered through silica gel to afford an oil, 4.835 g (100% yield crude) as a mixture of diastereomers

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

Procedure: To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet were added 8.14 g (28.36 mmol) ethyl-N-benzyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 60 mL ethanol, 8.93 g (141.8 mmol) ammonium formate, and 5 g 10% palladium-on-carbon. The reaction was refluxed and fresh catalyst and ammonium formate were added until the starting material disappeared (about 4 hr, a total of 8 g catalyst). The reaction was cooled, filtered through diatomaceous earth (Celite [trademark]), and evaporated. The residue was partitioned between methylene chloride and an aqueous sodium hydroxide solution, and the organic layer separated, dried over sodium sulfate, and evaporated. The resulting oil was used directly in the next step. To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet The reaction was refluxed about 4 hr The reaction was cooled filtered through diatomaceous earth (Celite [trademark]) evaporated The residue was partitioned between methylene chloride an aqueous sodium hydroxide solution, and the organic layer separated dried over sodium sulfate evaporated

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

Procedure: To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet were added 5.59 g (28.36 mmol) ethyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 142 mL ethanol, and 9.47 g (56.72 mmol) ethyl bromoacetate. The reaction was refluxed 3 days, cooled, and evaporated. The residue was partitioned between methylene chloride and aqueous sodium hydroxide, and the organic layer was dried over sodium sulfate and evaporated. The residue was filtered through silica gel using ethyl acetate to afford an oil, 4,835 g (100% yield crude), as a mixture of diastereomers. To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet The reaction was refluxed 3 days cooled evaporated The residue was partitioned between methylene chloride and aqueous sodium hydroxide the organic layer was dried over sodium sulfate evaporated The residue was filtered through silica gel to afford an oil, 4,835 g (100% yield crude) as a mixture of diastereomers