Aluminium lithium hydride → HCID 86751499, compound

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Reaction Steps

To a stirred solution of the compound from step A in THF (0.1M) at 0° C. was added LiAlH4 (1M in ether, 2.2 eq) dropwise over 10 minutes. The mixture was warmed to room temperature and stirred for 12 hours. The mixture was cooled to 0° C., quenched with Rochelles salt, and filtered through diatomaceous earth. The aqueous layer was extracted twice with ethylacetate, and the combined organic layers were washed with brine and dried over MgSO4. Filtration an solvent removal afforded a yellow oil. Chromatography over silica gel (ethylacetate:hexane) afforded a 60% yield of a white solid. M.P. 65°-70° C. (decomposed). Anal. calcd. for C27H26 NO3F: C, 75.15; H, 6.07; N, 3.25. Found: C, 74.75, H, 6.02, N, 3.09. 1H-NMR (300 MHz, CDCl3) :7.70 (1H, dd), 7.02-7.37 (8H, m), 6.96 (1H, dd), 7.91 (1H, d), 4.51 (1H, d), 4.23 (1H, dd), 4.39 (1H, dd) 3.87 (2H, dd), 2.74 (1H, dd), 2.55 (1H, dd), 2.18-2.28 (1H, m) 1.31 (6 H, d).

Provenance & Evidence