2-methyl-N-(trimethylsilylmethyl)propan-2-amine

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

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

Procedure: N-tert-Butyl-N-(trimethylsilylmethyl)amine 77 (8.47 g, 53.1 mmol) was added dropwise, over approximately 30 min, via a pressure equalizing addition funnel to a stirred solution of aqueous formaldehyde (5.98 mL of a 37 wt. % solution in water, 79.7 mmol) at 0° C. After 45 min, methanol (6.45 mL, 159.3 mmol) was added and the resulting solution was saturated with potassium carbonate. After stirring vigorously for approximately 5 h, the aqueous phase was removed. The organic phase was saturated with potassium carbonate and stirred overnight. The reaction mixture was poured into water and extracted three times with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4) and the volatiles evaporated in vacuo. Distillation (high vacuum; ˜70° C.) of the residual liquid afforded the title compound 78 as a colorless liquid. at 0° C the aqueous phase was removed stirred overnight The reaction mixture was poured into water extracted three times with diethyl ether The combined organic extracts were washed with brine dried (MgSO4) the volatiles evaporated in vacuo Distillation (high vacuum; ˜70° C.) of the residual liquid

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of tert-butylamine (18.0 mL, 171 mmol) and (chloromethyl)trimethylsilane (7.00 g, 57.1 mmol) was heated in a thick-walled glass tube at 200° C. overnight. After cooling to ambient temperature, the reaction mixture was poured into 1 N NaOH and extracted three times with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4), and the volatiles evaporated in vacuo. Distillation (atmospheric pressure; ˜135° C.) of the residual liquid gave the title compound 77 as a colorless liquid. After cooling to ambient temperature extracted three times with diethyl ether The combined organic extracts were washed with brine dried (MgSO4) the volatiles evaporated in vacuo Distillation (atmospheric pressure; ˜135° C.) of the residual liquid

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

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

Procedure: N-tert-Butyl-N-(trimethylsilylmethyl)amine 77 (8.47 g, 53.1 mmol) was added dropwise, over approximately 30 min, via a pressure equalizing addition funnel to a stirred solution of aqueous formaldehyde (5.98 mL of a 37 wt. % solution in water, 79.7 mmol) at 0° C. After 45 min, methanol (6.45 mL, 159.3 mmol) was added and the resulting solution was saturated with potassium carbonate. After stirring vigorously for approximately 5 h, the aqueous phase was removed. The organic phase was saturated with potassium carbonate and stirred overnight. The reaction mixture was poured into water and extracted three times with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4) and the volatiles evaporated in vacuo. Distillation (high vacuum; ˜70° C.) of the residual liquid afforded the title compound 78 as a colorless liquid. at 0° C the aqueous phase was removed stirred overnight The reaction mixture was poured into water extracted three times with diethyl ether The combined organic extracts were washed with brine dried (MgSO4) the volatiles evaporated in vacuo Distillation (high vacuum; ˜70° C.) of the residual liquid

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of tert-butylamine (18.0 mL, 171 mmol) and (chloromethyl)trimethylsilane (7.00 g, 57.1 mmol) was heated in a thick-walled glass tube at 200° C. overnight. After cooling to ambient temperature, the reaction mixture was poured into 1 N NaOH and extracted three times with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4), and the volatiles evaporated in vacuo. Distillation (atmospheric pressure; ˜135° C.) of the residual liquid gave the title compound 77 as a colorless liquid. After cooling to ambient temperature extracted three times with diethyl ether The combined organic extracts were washed with brine dried (MgSO4) the volatiles evaporated in vacuo Distillation (atmospheric pressure; ˜135° C.) of the residual liquid

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

Procedure: N-tert-Butyl-N-(trimethylsilylmethyl)amine (N-1) (8.47 g, 53.1 mmol) was added dropwise, over approximately 30 min, via a pressure equalizing addition funnel to a stirred solution of aqueous formaldehyde (5.98 mL of a 37 wt. % solution in water, 79.7 mmol) at 0° C. (ice cooling). After 45 min, methanol (6.45 mL, 159.3 mmol) was added and the resulting solution was saturated with potassium carbonate. After stirring vigorously for approximately 5 h, the aqueous phase was removed. The organic phase was saturated with potassium carbonate and stirred overnight. The reaction mixture was poured into water and extracted three times with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4) and the volatiles evaporated in vacuo. Distillation (high vacuum; ˜70° C.) of the residual liquid afforded the title compound as a colorless liquid (3.50 g). at 0° C. the aqueous phase was removed stirred overnight The reaction mixture was poured into water extracted three times with diethyl ether The combined organic extracts were washed with brine dried (MgSO4) the volatiles evaporated in vacuo Distillation (high vacuum; ˜70° C.) of the residual liquid

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of tert-butylamine (18.0 mL, 171 mmol) and (chloromethyl)trimethylsilane (7.00 g, 57.1 mmol) was heated in a thick-walled glass tube at 200° C. overnight. After cooling to ambient temperature, the reaction mixture was poured into 1 N NaOH and extracted three times with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4), and the volatiles evaporated in vacuo. Distillation (atmospheric pressure; ˜135° C.) of the residual liquid gave the title compound as a colorless liquid (7.67 g). After cooling to ambient temperature extracted three times with diethyl ether The combined organic extracts were washed with brine dried (MgSO4) the volatiles evaporated in vacuo Distillation (atmospheric pressure; ˜135° C.) of the residual liquid

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of tert-butylamine (18.0 mL, 171 mmol) and (chloromethyl)trimethylsilane (7.00 g, 57.1 mmol) was heated in a thick-walled glass tube at 200° C. overnight. After cooling to ambient temperature, the reaction mixture was poured into 1 N NaOH and extracted three times with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4), and the volatiles evaporated in vacuo. Distillation (atmospheric pressure; ˜135° C.) of the residual liquid gave the title compound as a colorless liquid (7.67 g). After cooling to ambient temperature extracted three times with diethyl ether The combined organic extracts were washed with brine dried (MgSO4) the volatiles evaporated in vacuo Distillation (atmospheric pressure; ˜135° C.) of the residual liquid

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of tert-butylamine (18.0 mL, 171 mmol) and (chloromethyl)trimethylsilane (7.00 g, 57.1 mmol) was heated in a thick-walled glass tube at 200° C. overnight. After cooling to ambient temperature, the reaction mixture was poured into 1 N NaOH and extracted three times with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4), and the volatiles evaporated in vacuo. Distillation (atmospheric pressure; ˜135° C.) of the residual liquid gave the title compound as a colorless liquid (7.67 g). After cooling to ambient temperature extracted three times with diethyl ether The combined organic extracts were washed with brine dried (MgSO4) the volatiles evaporated in vacuo Distillation (atmospheric pressure; ˜135° C.) of the residual liquid

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

Procedure: N-tert-Butyl-N-(trimethylsilylmethyl)amine 1-1 (8.47 g, 53.1 mmol) was added dropwise, over approximately 30 min, via a pressure equalizing addition funnel to a stirred solution of aqueous formaldehyde (5.98 mL of a 37 wt. % solution in water, 79.7 mmol) at 0° C. After 45 min, methanol (6.45 mL, 159.3 mmol) was added and the resulting solution was saturated with potassium carbonate. After stirring vigorously for approximately 5 h, the aqueous phase was removed. The organic phase was saturated with potassium carbonate and stirred overnight. The reaction mixture was poured into water and extracted three times with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4) and the volatiles evaporated in vacuo. Distillation (high vacuum; ˜70° C.) of the residual liquid afforded the title compound 1-2 as a colorless liquid. at 0° C the aqueous phase was removed stirred overnight The reaction mixture was poured into water extracted three times with diethyl ether The combined organic extracts were washed with brine dried (MgSO4) the volatiles evaporated in vacuo Distillation (high vacuum; ˜70° C.) of the residual liquid

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of tert-butylamine (18.0 mL, 171 mmol) and (chloromethyl)trimethylsilane (7.00 g, 57.1 mmol) was heated in a thick-walled glass tube at 200° C. overnight After cooling to ambient temperature, the reaction mixture was poured into 1 N NaOH and extracted three times with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4), and the volatiles evaporated in vacuo. Distillation (atmospheric pressure; ˜135° C.) of the residual liquid gave the title compound 1-1 as a colorless liquid. After cooling to ambient temperature extracted three times with diethyl ether The combined organic extracts were washed with brine dried (MgSO4) the volatiles evaporated in vacuo Distillation (atmospheric pressure; ˜135° C.) of the residual liquid