trimethyl methanetricarboxylate

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

Procedure: A concentrated hydrochloric acid was added to a mixture of cyclooctanone (3.84 g, 30.43 mmol) and butylamine (3.01 mL, 30.43 mmol) by two drops, and the mixture was stirred at room temperature for 15 hours. Diluted sodium carbonate aqueous solution and ethyl acetate were added in the reaction mixture to separate the mixture, and the organic layer was washed with water and saturated saline. After the organic layer had been dried, the solvent was removed by distillation and 4.72 g of colorless oily matter was obtained (86%). This imine (4.67 g, 25.76 mmol) was reacted as mentioned above together with trimethylmethane tricarboxylic acid (3.42 g, 18 mM) in trigrim (40 mL), and viscous yellow oily matter (AA17, 2.62 g, 47%) was obtained. to separate the mixture the organic layer was washed with water and saturated saline After the organic layer had been dried the solvent was removed by distillation and 4.72 g of colorless oily matter was obtained (86%) was obtained

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

Procedure: A concentrated hydrochloric acid was added to a mixture of cyclooctanone (3.84 g, 30.43 mmol) and butylamine (3.01 mL, 30.43 mmol) by two drops, and the mixture was stirred at room temperature for 15 hours. Diluted sodium carbonate aqueous solution and ethyl acetate were added in the reaction mixture to separate the mixture, and the organic layer was washed with water and saturated saline. After the organic layer had been dried, the solvent was removed by distillation and 4.72 g of colorless oily matter was obtained (86%). This imine (4.67 g, 25.76 mmol) was reacted as mentioned above together with trimethylmethane tricarboxylic acid (3.42 g, 18 mM) in trigrim (40 mL), and viscous yellow oily matter (AA17, 2.62 g, 47%) was obtained. to separate the mixture the organic layer was washed with water and saturated saline After the organic layer had been dried the solvent was removed by distillation and 4.72 g of colorless oily matter was obtained (86%) was obtained

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

Procedure: A concentrated hydrochloric acid was added to a mixture of cyclooctanone (3.84 g, 30.43 mmol) and butylamine (3.01 mL, 30.43 mmol) by two drops, and the mixture was stirred at room temperature for 15 hours. Diluted sodium carbonate aqueous solution and ethyl acetate were added in the reaction mixture to separate the mixture, and the organic layer was washed with water and saturated saline. After the organic layer had been dried, the solvent was removed by distillation and 4.72 g of colorless oily matter was obtained (86%). This imine (4.67 g, 25.76 mmol) was reacted as mentioned above together with trimethylmethane tricarboxylic acid (3.42 g, 18 mM) in trigrim (40 mL), and viscous yellow oily matter (AA17, 2.62 g, 47%) was obtained. to separate the mixture the organic layer was washed with water and saturated saline After the organic layer had been dried the solvent was removed by distillation and 4.72 g of colorless oily matter was obtained (86%) was obtained

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

Procedure: A solution of N-(1-(1-(tert-butyldimethylsilyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)butylidene)-2-methylpropan-2-amine (3.8 g, 9.0 mmol) and trimethyl methanetricarboxylate (2.6 g. 13.5 mmol) in Ph2O (10 mL) was heated at 220° C. for 30 min. The reaction mixture was then cooled to room temperature and triturated with Et2O to afford the title compound as an off-white solid (1.2 g, 30%). triturated with Et2O

Conditions: temp:230.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(1-(2-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1H-indol-5-yl)butylidene)-2-methylpropan-2-amine (2.10 g, ca. 5.2 mmol), prepared according to procedure described in Example 39 Step 5, in Ph2O (5 mL) was added trimethyl methanetricarboxylate (1.68 g, 8.8 mmol, 1.7 eq). The mixture was heated to 230° C. for 2 h. The mixture was cooled to room temperature then purified by flash column chromatography (0-50% EtOAc in CH2Cl2) to afford the title compound (0.51 g, 1.1 mmol, 21%) as a light yellow solid. LC-MS 469.2 [M−H]−, 471.2 [M+H]+, RT 1.67 min. The mixture was cooled to room temperature then purified by flash column chromatography (0-50% EtOAc in CH2Cl2)

Conditions: temp:230.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 2-methyl-N-(1-(1-methyl-1H-indol-5-yl)butylidene)propan-2-amine (6.70 g, ca. 26.1 mmol), prepared according to procedure described in Example 21 Step 2, in Ph2O (40 mL) was added trimethyl methanetricarboxylate (8.44 g, 44.4 mmol, 1.7 eq). Distillation apparatus was set up then attached to the flask. The reaction was stirred at 230° C. for 10 min then heating was removed. The mixture was cooled to room temperature. The precipitate was collected by filtration then washed with diethyl ether to afford the title compound as a yellow solid (4.85 g, 14.9 mmol, 55%). prepared Distillation apparatus then heating was removed The mixture was cooled to room temperature The precipitate was collected by filtration then washed with diethyl ether

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 2-methyl-N-(1-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)butylidene)propan-2-amine (1.96 g, ca. 7.2 mmol), prepared according to procedure described in Example 1 Step 6, in diglyme (7 mL) was added trimethyl methanetricarboxylate (2.33 g, 12.2 mmol, 1.7 eq). The reaction was stirred at 160° C. for 4 h then cooled to room temperature. The precipitate was collected by filtration then washed with Et2O to afford the title compound as a yellow solid (150 mg, 0.44 mmol, 6.5% over two steps). prepared then cooled to room temperature The precipitate was collected by filtration then washed with Et2O

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

Procedure: A concentrated hydrochloric acid was added to a mixture of cyclooctanone (3.84 g, 30.43 mmol) and butylamine (3.01 mL, 30.43 mmol) by two drops, and the mixture was stirred at room temperature for 15 hours. Diluted sodium carbonate aqueous solution and ethyl acetate were added in the reaction mixture to separate the mixture, and the organic layer was washed with water and saturated saline. After the organic layer had been dried, the solvent was removed by distillation and 4.72 g of colorless oily matter was obtained (86%). This imine (4.67 g, 25.76 mmol) was reacted as mentioned above together with trimethylmethane tricarboxylic acid (3.42 g, 18 mM) in trigrim (40 mL), and viscous yellow oily matter (AA17, 2.62 g, 47%) was obtained. to separate the mixture the organic layer was washed with water and saturated saline After the organic layer had been dried the solvent was removed by distillation and 4.72 g of colorless oily matter was obtained (86%) was obtained