Formaldehyde → N-tert-Butyl-N-(methoxymethyl)-N-(trimethylsilylmethyl)amine

Participants

Reaction Conditions

Reaction Steps

2-Methyl-N-[(trimethylsilyl)methyl]propan-2-amine (from preparation 5) (4.31 g, 27 mmol) was added to an ice-cooled mixture of methanol (1.29 mL, 31.8 mmol) and aqueous formaldehyde (37% w/v 2.49 mL, 33 mmol) over 45 minutes. The heterogeneous mixture was stirred at 0° C. for 2 hours and then solid potassium carbonate (325 mesh) (1.08 g, 13 mmol) was added and the mixture stirred for 30 minutes at 0° C. The layers were separated and the aqueous phase extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered, and evaporated under reduced pressure to give an 80:20 mixture of the title compound and unreacted tert-butyl[(trimethylsilyl)methyl]amine as a colourless oil (5.09 g). The mixture was used directly without further purification in preparation 2.

Provenance & Evidence