3-methyl-3,9-diazaspiro[5.5]undecane

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Was prepared according to method A from 3-methyl-3,9-diaza-spiro[5.5]undecane and 1-bromo-3,4-dichlorobenzene as a yellow oil. LC-ESI−HRMS of [M+H]+ shows 313.1238 Da. Calc. 313.123829 Da, dev. −0.1 ppm. Was prepared

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

Procedure: 9-Methyl-3,9-diaza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (435 mg, 1.62 mmol) was dissolved in dichloromethane (11 mL) and cooled on ice. Trifluoroacetic acid (4 mL) in dichloromethane (5 mL) was added and the reaction mixture was stirred at room temperature for 2 h. Evaporation to dryness, co-evaporation with toluene, ethyl acetate and diethyl ether gave a foam which was dissolved in dichloromethane, and sodium hydroxide (2 N) was added. The aqueous phase was extracted five times with dichloromethane. The combined organic phase was washed with brine, dried (sodium sulfate), filtered and evaporated to give 214 mg (78%) of 3-methyl-3,9-diaza-spiro[5.5]undecane. cooled on ice Evaporation to dryness, co-evaporation with toluene, ethyl acetate and diethyl ether gave a foam which The aqueous phase was extracted five times with dichloromethane The combined organic phase was washed with brine dried (sodium sulfate) filtered evaporated

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Was prepared according to method A from 3-methyl-3,9-diaza-spiro[5.5]undecane and 1-bromo-3,4-dichlorobenzene as a yellow oil. LC-ESI−HRMS of [M+H]+ shows 313.1238 Da. Calc. 313.123829 Da, dev. −0.1 ppm. Was prepared

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

Procedure: 9-Methyl-3,9-diaza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (435 mg, 1.62 mmol) was dissolved in dichloromethane (11 mL) and cooled on ice. Trifluoroacetic acid (4 mL) in dichloromethane (5 mL) was added and the reaction mixture was stirred at room temperature for 2 h. Evaporation to dryness, co-evaporation with toluene, ethyl acetate and diethyl ether gave a foam which was dissolved in dichloromethane, and sodium hydroxide (2 N) was added. The aqueous phase was extracted five times with dichloromethane. The combined organic phase was washed with brine, dried (sodium sulfate), filtered and evaporated to give 214 mg (78%) of 3-methyl-3,9-diaza-spiro[5.5]undecane. cooled on ice Evaporation to dryness, co-evaporation with toluene, ethyl acetate and diethyl ether gave a foam which The aqueous phase was extracted five times with dichloromethane The combined organic phase was washed with brine dried (sodium sulfate) filtered evaporated