N-[2-(t-butyldiphenylsilyloxy)ethyl]-N-methyl-carbamic acid benzyl ester → 2-(tert-butyldiphenylsilyloxy)-N-methylethanamine

Participants

Reaction Steps

A solution of N-[2-(t-butyldiphenylsilyloxy)-ethyl]-N-methyl-carbamic acid benzyl ester (5.7 g, 12.7 mmol) (obtained as described in Reference Example 40(1)) in methanol (285 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium on charcoal (5.7 g) at room temperature. After checking the completion of the reaction, the reaction mixture was filtered in order to remove the catalyst and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (19:2)→ethyl acetate:methanol (1:1) as the eluant to afford [2-(t-butyldiphenylsilyloxy)ethyl]methylamine (2.67 g, yield 69%) as a transparent oil.

Provenance & Evidence