(2S,6S)-2,6-dimethylpiperidin-4-one

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

Procedure: trans-2,6-Dimethylpiperidin-4-one (93; 5.2 g, 39 mmol) was dissolved in CH2Cl2 (100 mL) and triethylamine (22 mL, 155 mmol) was added. The solution was stirred and treated with 4-chlorobenzenesulfonyl chloride (9.2 g, 43 mmol). The mixture was stirred for 24 hr and then partitioned between water (300 mL) and CH2Cl2 (300 mL). The organic layer was washed with 0.2 N citric acid, water, brine, dried over Na2SO4, filtered and the solvent evaporated. The residue (6.7 g) was purified by flash chromatography, eluting with EtOAc-hexane (1:3) mixture to yield 3.6 g (35%, 2 steps) of product 94. The mixture was stirred for 24 hr partitioned between water (300 mL) and CH2Cl2 (300 mL) The organic layer was washed with 0.2 N citric acid, water, brine dried over Na2SO4 filtered the solvent evaporated The residue (6.7 g) was purified by flash chromatography eluting with EtOAc-hexane (1:3) mixture

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

Procedure: trans-N-Benzyl-2,6-dimethylpiperidin-4-one (91; 7.5 g) was dissolved in EtOH (20 mL) and the catalyst (0.8 g, Pd/C5%) was added. The slurry was vigorously stirred and kept under a hydrogen atmosphere (60 psi) for 90 hr. The catalyst was removed by filtration through Celite and the filtrate was evaporated at 3 mmHg/40° C. The residue (ca. 5.2 g) was used without further purification. for 90 hr The catalyst was removed by filtration through Celite the filtrate was evaporated at 3 mmHg/40° C The residue (ca. 5.2 g) was used without further purification

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

Procedure: trans-2,6-Dimethylpiperidin-4-one (93; 5.2 g, 39 mmol) was dissolved in CH2Cl2 (100 mL) and triethylamine (22 mL, 155 mmol) was added. The solution was stirred and treated with 4-chlorobenzenesulfonyl chloride (9.2 g, 43 mmol). The mixture was stirred for 24 hr and then partitioned between water (300 mL) and CH2Cl2 (300 mL). The organic layer was washed with 0.2 N citric acid, water, brine, dried over Na2SO4, filtered and the solvent evaporated. The residue (6.7 g) was purified by flash chromatography, eluting with EtOAc-hexane (1:3) mixture to yield 3.6 g (35%, 2 steps) of product 94. The mixture was stirred for 24 hr partitioned between water (300 mL) and CH2Cl2 (300 mL) The organic layer was washed with 0.2 N citric acid, water, brine dried over Na2SO4 filtered the solvent evaporated The residue (6.7 g) was purified by flash chromatography eluting with EtOAc-hexane (1:3) mixture

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

Procedure: trans-N-Benzyl-2,6-dimethylpiperidin-4-one (91; 7.5 g) was dissolved in EtOH (20 mL) and the catalyst (0.8 g, Pd/C5%) was added. The slurry was vigorously stirred and kept under a hydrogen atmosphere (60 psi) for 90 hr. The catalyst was removed by filtration through Celite and the filtrate was evaporated at 3 mmHg/40° C. The residue (ca. 5.2 g) was used without further purification. for 90 hr The catalyst was removed by filtration through Celite the filtrate was evaporated at 3 mmHg/40° C The residue (ca. 5.2 g) was used without further purification

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

Procedure: trans-2,6-Dimethylpiperidin-4-one (93; 5.2 g, 39 mmol) was dissolved in CH2Cl2 (100 mL) and triethylamine (22 mL, 155 mmol) was added. The solution was stirred and treated with 4-chlorobenzenesulfonyl chloride (9.2 g, 43 mmol). The mixture was stirred for 24 hr and then partitioned between water (300 mL) and CH2Cl2 (300 mL). The organic layer was washed with 0.2 N citric acid, water, brine, dried over Na2SO4, filtered and the solvent evaporated. The residue (6.7 g) was purified by flash chromatography, eluting with EtOAc-hexane (1:3) mixture to yield 3.6 g (35%, 2 steps) of product 94. The mixture was stirred for 24 hr partitioned between water (300 mL) and CH2Cl2 (300 mL) The organic layer was washed with 0.2 N citric acid, water, brine dried over Na2SO4 filtered the solvent evaporated The residue (6.7 g) was purified by flash chromatography eluting with EtOAc-hexane (1:3) mixture

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

Procedure: trans-N-Benzyl-2,6-dimethylpiperidin-4-one (91; 7.5 g) was dissolved in EtOH (20 mL) and the catalyst (0.8 g, Pd/C5%) was added. The slurry was vigorously stirred and kept under a hydrogen atmosphere (60 psi) for 90 hr. The catalyst was removed by filtration through Celite and the filtrate was evaporated at 3 mmHg/40° C. The residue (ca. 5.2 g) was used without further purification. for 90 hr The catalyst was removed by filtration through Celite the filtrate was evaporated at 3 mmHg/40° C The residue (ca. 5.2 g) was used without further purification