N-(Methoxymethyl)-1,1-diphenyl-N-[(trimethylsilyl)methyl]methanamine

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Diphenyl-N-((trimethylsilyl)methyl)methanamine (5.5 g, 20.4 mmol) was added dropwise to mixture of 37% aqueous formaldehyde (2.9 g) and methanol (1.5 g) while stirring at 0° C. After the addition was complete the reaction mixture was stirred for 2 hours at 0° C. K2CO3 (3 g) was added and the solidified mixture was warmed to room temperature. Methanol (4 ml) was added. After one hour stirring at room temperature, tBME (50 ml) and water (5 ml) was added. The organic layer was separated and dried with Na2SO4. Evaporation under vacuum gave the crude product N-(methoxymethyl)diphenyl-N-((trimethylsilyl)methyl)methanamine (7.05 g, max. 20.4 mmol) as an oil, which solidified on standing overnight at room temperature. The product was used without further purification. After the addition was stirred for 2 hours at 0° C the solidified mixture was warmed to room temperature After one hour stirring at room temperature The organic layer was separated dried with Na2SO4 Evaporation under vacuum

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Diphenyl-N-((trimethylsilyl)methyl)methanamine (5.5 g, 20.4 mmol) was added dropwise to mixture of 37% aqueous formaldehyde (2.9 g) and methanol (1.5 g) while stirring at 0° C. After the addition was complete the reaction mixture was stirred for 2 hours at 0° C. K2CO3 (3 g) was added and the solidified mixture was warmed to room temperature. Methanol (4 ml) was added. After one hour stirring at room temperature, tBME (50 ml) and water (5 ml) was added. The organic layer was separated and dried with Na2SO4. Evaporation under vacuum gave the crude product N-(methoxymethyl)diphenyl-N-((trimethylsilyl)methyl)methanamine (7.05 g, max. 20.4 mmol) as an oil, which solidified on standing overnight at room temperature. The product was used without further purification. After the addition was stirred for 2 hours at 0° C the solidified mixture was warmed to room temperature After one hour stirring at room temperature The organic layer was separated dried with Na2SO4 Evaporation under vacuum