3,4,4a,5,6,7,8,8a-octahydro-2H-naphthalen-1-one

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: A mixture of 64 parts of octahydro-1(2H)-naphthalenone, 50 parts of methyl glycine hydrochloride, 2 parts of a solution of thiophene in methanol 4%, 560 parts of methanol and 50 parts of potassium acetate was hydrogenated at normal pressure and at room temperature with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in a mixture of water and trichloromethane. The whole was treated with a sodium hydroxide solution. The separated organic layer was dried, filtered and evaporated, yielding 82.2 parts (91.1%) of methyl N-(decahydro-1-naphthalenyl)glycine as a residue (intermediate 1). the catalyst was filtered off the filtrate was evaporated The residue was taken up in a mixture of water and trichloromethane The whole was treated with a sodium hydroxide solution The separated organic layer was dried filtered evaporated

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: A suspension of sodium hydride (4.60 g, 115 mmol) in tetrahydrofuran (20 mL) was treated with dimethyl carbonate (8.29 mL, 99 mmol), heated to reflux under nitrogen, treated dropwise with a solution of octahydronaphthalen-1(2H)-one (Aldrich cat#115063, mixture of trans (major) and cis (minor), 5 g, 32.8 mmol) in tetrahydrofuran (20 mL) over 5 minutes, and heated to reflux overnight. The mixture was cooled, diluted with ether (300 mL) and treated with 1 M hydrochloric acid (150 mL). The layers were separated and the aqueous layer was extracted with ether (2×100 mL). The combined ether layers were washed with brine, dried (magnesium sulfate), filtered and concentrated to provide the desired product that was not purified, but used as is in the next step. heated to reflux under nitrogen heated to reflux overnight The mixture was cooled The layers were separated the aqueous layer was extracted with ether (2×100 mL) The combined ether layers were washed with brine dried (magnesium sulfate) filtered concentrated

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

Procedure: A mixture of 64 parts of octahydro-1(2H)-naphthalenone, 50 parts of methyl glycine hydrochloride, 2 parts of a solution of thiophene in methanol 4%, 560 parts of methanol and 50 parts of potassium acetate was hydrogenated at normal pressure and at room temperature with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in a mixture of water and trichloromethane. The whole was treated with a sodium hydroxide solution. The separated organic layer was dried, filtered and evaporated, yielding 82.2 parts (91.1%) of methyl N-(decahydro-1-naphthalenyl)glycine as a residue (intermediate 1). the catalyst was filtered off the filtrate was evaporated The residue was taken up in a mixture of water and trichloromethane The whole was treated with a sodium hydroxide solution The separated organic layer was dried filtered evaporated