4-Nitrophenol → HCID 86585802, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.), stirred solution of triphenylphosphine (629 mg) in THF (6 mL) was added diisopropylazodicarboxylate (0.5 mL) dropwise and the resulting thick white slurry was stirred for 45 min. A solution of [2-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl]-(2-hydroxy-ethyl)-carbamic acid tert-butyl ester (515 mg) and 4-nitrophenol (332 mg) in THF (5 mL) was added dropwise to produce a yellow slurry. After an additional 1 h period, the cooling bath was removed and the mixture was allowed to stir at ambient temperature for 20 h. This mixture was concentrated in vacuo and chromatographed on a Biotage® F40M column (gradient of 10% to 15% ethyl acetate/hexanes) to afford 530 mg of the title compound (I-3c) as a colorless foam.

Provenance & Evidence