2,2-diethylbutan-1-amine

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

Procedure: Oxalyl chloride (COCl)2 (16.5 ml, 188 mmol) in methylene chloride (150 ml) is cooled to −63°. DMSO (18 ml, 362 mmol) is then added dropwise. The resulting mixture is stirred for 30 minutes and then a mixture of 4-hydroxymethylbicyclo[2.2.2]octane-1-carboxylic acid benzyl ester (XVIII, Example 93, 34.5 g, 125 mmol) in methylene chloride (100 ml) is added over 15 minutes. After another 30 minutes, triethylethylamine (70 ml, 502 mmol) in methylene chloride (30 ml) is added over 25 minutes. (Extra Caution: extremely exothermic reaction when the first equivalent of the triethylamine is added.) The reaction mixture then stirred for another 45 minutes and the cooling bath is removed and allowed to warm up to 20-25°. Water (50 ml) is added and the organic layer is separated, dried over anhydrous sodium sulfate and concentrated to give the title compound, NMR (400 MHz, CDCl3) δ 9.51, 7.32, 5.11, 1.88 and 1.64. is added over 15 minutes After another 30 minutes is added ) The reaction mixture then stirred for another 45 minutes the cooling bath is removed to warm up to 20-25° Water (50 ml) is added the organic layer is separated dried over anhydrous sodium sulfate concentrated

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

Procedure: A mixture of 2-bromopropiophenone (21.3 g, 0.1M), imidazole (20.4 g, 0.3M), triethylethylamine (30.3 g, 0.3M) and ethyl acetate (300 ml) was refluxed overnight, cooled to room temperature and treated with water. The organic phase was separated, dried over MgSO4 and evaporated to give 2-(imidazol-1-yl)propiophenone as a viscous oil (12.95 g, was refluxed overnight The organic phase was separated dried over MgSO4 evaporated

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

Procedure: A mixture of 2-bromopropiophenone (21.3 g, 0.1M), imidazole (20.4 g, 0.3M), triethylethylamine (30.3 g, 0.3M) and ethyl acetate (300 ml) was refluxed overnight, cooled to room temperature and treated with water. The organic phase was separated, dried over MgSO4 and evaporated to give 2-(imidazol-1-yl)propiophenone as a viscous oil (12.95 g, was refluxed overnight The organic phase was separated dried over MgSO4 evaporated

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

Procedure: Oxalyl chloride (COCl)2 (16.5 ml, 188 mmol) in methylene chloride (150 ml) is cooled to −63°. DMSO (18 ml, 362 mmol) is then added dropwise. The resulting mixture is stirred for 30 minutes and then a mixture of 4-hydroxymethylbicyclo[2.2.2]octane-1-carboxylic acid benzyl ester (XVIII, Example 93, 34.5 g, 125 mmol) in methylene chloride (100 ml) is added over 15 minutes. After another 30 minutes, triethylethylamine (70 ml, 502 mmol) in methylene chloride (30 ml) is added over 25 minutes. (Extra Caution: extremely exothermic reaction when the first equivalent of the triethylamine is added.) The reaction mixture then stirred for another 45 minutes and the cooling bath is removed and allowed to warm up to 20-25°. Water (50 ml) is added and the organic layer is separated, dried over anhydrous sodium sulfate and concentrated to give the title compound, NMR (400 MHz, CDCl3) δ 9.51, 7.32, 5.11, 1.88 and 1.64. is added over 15 minutes After another 30 minutes is added ) The reaction mixture then stirred for another 45 minutes the cooling bath is removed to warm up to 20-25° Water (50 ml) is added the organic layer is separated dried over anhydrous sodium sulfate concentrated

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

Procedure: Oxalyl chloride (COCl)2 (16.5 ml, 188 mmol) in methylene chloride (150 ml) is cooled to −63°. DMSO (18 ml, 362 mmol) is then added dropwise. The resulting mixture is stirred for 30 minutes and then a mixture of 4-hydroxymethylbicyclo[2.2.2]octane-1-carboxylic acid benzyl ester (XVIII, Example 93, 34.5 g, 125 mmol) in methylene chloride (100 ml) is added over 15 minutes. After another 30 minutes, triethylethylamine (70 ml, 502 mmol) in methylene chloride (30 ml) is added over 25 minutes. (Extra Caution: extremely exothermic reaction when the first equivalent of the triethylamine is added.) The reaction mixture then stirred for another 45 minutes and the cooling bath is removed and allowed to warm up to 20-25°. Water (50 ml) is added and the organic layer is separated, dried over anhydrous sodium sulfate and concentrated to give the title compound, NMR (400 MHz, CDCl3) δ 9.51, 7.32, 5.11, 1.88 and 1.64. is added over 15 minutes After another 30 minutes is added ) The reaction mixture then stirred for another 45 minutes the cooling bath is removed to warm up to 20-25° Water (50 ml) is added the organic layer is separated dried over anhydrous sodium sulfate concentrated