Tetrahydrofuran → HCID 57705999, compound

Participants

Reaction Steps

To a stirred solution of 1-(2′-fluoro-4-(hydroxymethyl)-5′-(methyloxy)-1,1′-biphenyl-2-yl)-2,2-dimethyl-1-propanone T9.6 (2.00 g, 6.3 mmol) in THF (63 mL, 6.3 mmol) at 0° C. was added LAH (1.0 M in THF, 13 mL, 13 mmol). Stirring was continued for 2 hours. 1N NaOH (aq) was added to the mixture, and the resulting mixture was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give the residue. The residue was purified by silica gel flash chromatography (0-30% EtOAc/hexane) to afford 1-(2′-fluoro-4-(hydroxymethyl)-5′-(methyloxy)-1,1′-biphenyl-2-yl)-2,2-dimethyl-1-propanol T9.7 (1.50 g, 75% yield) as a white solid. MS ESI (pos.) m/e: 336.2 (M+H2O)+. Chiral separation of T9.7 was accomplished on Chiracel-OD (4% IPA in hexane) to provide T9.8 and T9.9. Analytical column (Chiracel-OD (4% IPA in hexane, 45 min run) peak 1—18.5 mins, peak 2—24.5 mins).1

Provenance & Evidence