HCID 11521987, compound → HCID 53784530, compound

Participants

Reaction Conditions

Reaction Steps

To 56 mg (200 μmole) (12), prepared in Step 1, above, was added 2 mL of dry Et2O, and the solution was cooled to 0° C. Lithium aluminum hydride (9.5 mg, 50 μmole, 1.25 eq. H-) was added, and the reaction was monitored by TLC. After 2 h the reaction was quenched with ca. 4 mL ethyl acetate and the solution stirred for 40 min. The organic layer was washed 2× with dilute HCl, 2× with saturated NaHCO3, and 1× with brine. The organic layer was dried with Na2SO4, filtered, and the filtrate evaporated. The residue was pumped on high vacuum overnight, then purified by flash silica gel chromatography to give the title compound. NMR (300 MHz, CDCl3): δ 9.60 (s, CHO, 1H), 7.20 (m, Ph, 5H), 4.45 (br dd, Phe-α, 1H), 4.08 (q, CH3CH2OCO, 2H), 3.08 (d, Phe-β, 2H), 1.20 (t, CH3CH2OCO, 3H).

Provenance & Evidence