Acetic Acid → HCID 58841404, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (7-cyano-chroman-4-yl)-methyl-carbamic acid tert-butyl ester (299 mg, 1.04 mmol, 1.0 eq) in anhydrous toluene (5 mL) under N2 at −20° C. was added diisobutylaluminum hydride (Aldrich, 1.50 M in toluene, 1.38 mL, 2.08 mmol, 2.0 eq) slowly. The reaction was stirred at −20° C. for 1 h. Glacial HOAc (1 mL) and H2O (5 mL) was added sequentially. The reaction was warmed to RT spontaneously and stirred at this temperature for an additional 1.5 h. A solution of saturated sodium potassium tartrate (50 mL) was added and the mixture was extracted with EtOAc (60 mL). The aqueous layer was adjusted to pH-10 with 2N NaOH, and extracted with EtOAc (60 mL×2). Combined organic phase was washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. Flash column chromatography (silica gel, 0-8% EtOAc-Hexane) afforded the title compound as a colorless sticky solid.

Provenance & Evidence