Ammonium formate → 4-{2(R)-[2-(tert-Butyl-dimethyl-silanyloxy)-2-pyridin-3-yl-ethylamino]-2-methyl-propyl}-phenylamine

Participants

Reaction Steps

To a slurry of [2(R)-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl]-[1,1-dimethyl-2-(4-nitro-phenyl)-ethyl]-amine (8.0 g) and 10% palladium-on-carbon (4.0 g) in MeOH (200 mL) was added ammonium formate (22 g) and the resulting mixture was stirred at ambient temperature for 3 h. The reaction mixture was filtered through Celite®, washing with MeOH and the filtrate concentrated in vacuo. The resulting semi-solid was partitioned between ethyl acetate and half-saturated aqueous sodium bicarbonate, the organic phase was separated, dried (Na2SO4) and concentrated in vacuo to afford 6.5 g of the title compound (I-2g) as a dark oil.

Provenance & Evidence