(3S,4S)-3-methyloxan-4-amine;hydrochloride

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

Procedure: Racemic cis 1-methanesulfonyl-3-methyl-piperidin-4-yl-amine was prepared in the same manner from racemic benzyl-(1-methanesulfonyl-3-methyl-piperidin-4-yl)-amine. In this instance, 1 atm H2 was used instead of 55 psi, and the HCl treatment was omitted.

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

Procedure: Racemic cis 1-methanesulfonyl-3-methyl-piperidin-4-yl-amine was prepared in the same manner from racemic benzyl-(1-methanesulfonyl-3-methyl-piperidin-4-yl)-amine. In this instance, 1 atm H2 was used instead of 55 psi, and the HCl treatment was omitted.

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

Procedure: Racemic cis 1-(4-amino-3-methyl-piperidin-1-yl)-ethanone was prepared in the same manner from racemic 1-acetyl-3-methyl-piperidin-4-one. In this instance, 1 atm H2 was used instead of 55 psi, and the HCl treatment was omitted.

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

Procedure: Racemic cis benzyl-(3-methyl-tetrahydro-pyran-4-yl)-amine (1.8 g, 8.768 mmol) was dissolved in 3M HCl (4.4 mL, 13.2 mmol). Pd(OH)2 20 wt % (0.6 g) and EtOH (50 mL) were added and the reaction mixture was hydrogenated in a Parr shaker at 55 psi H2 over the weekend. The palladium was filtered off. HCl 4M in dioxane was added and the solvent was evaporated. The remaining green oil was adsorbed onto SiO2 and purified by SiO2 chromatography (100 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 100-55% DCM). The fractions containing the product were combined and HCl 4M in dioxane was added. NH4Cl crashed out. The solvent was evaporated. The remaining white semi-solid was taken up in MeOH/Et2O and the salt was filtered off and washed with Et2O. The filtrate was evaporated. The remaining oil was taken up in DCM and was evaporated again to obtain 0.58 of racemic cis 3-methyl-tetrahydro-pyran-4-ylamine hydrochloride as a light yellow solid (43% yield). The palladium was filtered off HCl 4M in dioxane was added the solvent was evaporated purified by SiO2 chromatography (100 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 100-55% DCM) The fractions containing the product HCl 4M in dioxane was added The solvent was evaporated the salt was filtered off washed with Et2O The filtrate was evaporated was evaporated again

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

Procedure: Racemic cis benzyl-(3-methyl-tetrahydro-pyran-4-yl)-amine (1.8 g, 8.768 mmol) was dissolved in 3M HCl (4.4 mL, 13.2 mmol). Pd(OH)2 20 wt % (0.6 g) and EtOH (50 mL) were added and the reaction mixture was hydrogenated in a Parr shaker at 55 psi H2 over the weekend. The palladium was filtered off. HCl 4M in dioxane was added and the solvent was evaporated. The remaining green oil was adsorbed onto SiO2 and purified by SiO2 chromatography (100 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 100-55% DCM). The fractions containing the product were combined and HCl 4M in dioxane was added. NH4Cl crashed out. The solvent was evaporated. The remaining white semi-solid was taken up in MeOH/Et2O and the salt was filtered off and washed with Et2O. The filtrate was evaporated. The remaining oil was taken up in DCM and was evaporated again to obtain 0.58 of racemic cis 3-methyl-tetrahydro-pyran-4-ylamine hydrochloride as a light yellow solid (43% yield). The palladium was filtered off HCl 4M in dioxane was added the solvent was evaporated purified by SiO2 chromatography (100 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 100-55% DCM) The fractions containing the product HCl 4M in dioxane was added The solvent was evaporated the salt was filtered off washed with Et2O The filtrate was evaporated was evaporated again

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

Procedure: Racemic cis 1-methanesulfonyl-3-methyl-piperidin-4-yl-amine was prepared in the same manner from racemic benzyl-(1-methanesulfonyl-3-methyl-piperidin-4-yl)-amine. In this instance, 1 atm H2 was used instead of 55 psi, and the HCl treatment was omitted.

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

Procedure: Racemic cis 1-(4-amino-3-methyl-piperidin-1-yl)-ethanone was prepared in the same manner from racemic 1-acetyl-3-methyl-piperidin-4-one. In this instance, 1 atm H2 was used instead of 55 psi, and the HCl treatment was omitted.

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

Procedure: Racemic cis benzyl-(3-methyl-tetrahydro-pyran-4-yl)-amine (1.8 g, 8.768 mmol) was dissolved in 3M HCl (4.4 mL, 13.2 mmol). Pd(OH)2 20 wt % (0.6 g) and EtOH (50 mL) were added and the reaction mixture was hydrogenated in a Parr shaker at 55 psi H2 over the weekend. The palladium was filtered off. HCl 4M in dioxane was added and the solvent was evaporated. The remaining green oil was adsorbed onto SiO2 and purified by SiO2 chromatography (100 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 100-55% DCM). The fractions containing the product were combined and HCl 4M in dioxane was added. NH4Cl crashed out. The solvent was evaporated. The remaining white semi-solid was taken up in MeOH/Et2O and the salt was filtered off and washed with Et2O. The filtrate was evaporated. The remaining oil was taken up in DCM and was evaporated again to obtain 0.58 of racemic cis 3-methyl-tetrahydro-pyran-4-ylamine hydrochloride as a light yellow solid (43% yield). The palladium was filtered off HCl 4M in dioxane was added the solvent was evaporated purified by SiO2 chromatography (100 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 100-55% DCM) The fractions containing the product HCl 4M in dioxane was added The solvent was evaporated the salt was filtered off washed with Et2O The filtrate was evaporated was evaporated again