Ammonium Chloride → HCID 18433588, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-(tert-butoxycarbonylamino)-7-(triisopropylsilyloxy)-2-(trimethylsilyl)naphthalene, as described above in Step B, (9.72 g, 19.9 mmol) in THF (200 mL) at 0° C. was added TBAF (1.0 M in THF, 20.9 mL, 20.9 mmol). The resulting mixture was stirred at 0° C. for 15 min then poured into dilute aqueous NH4Cl (250 mL) and extracted with CH2Cl2 (500 mL). The organic extract was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with CH2Cl2—10% EtOAc to yield the desired product.

Provenance & Evidence