dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)-2-methylmalonate → methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-(hydroxymethyl)-2-methyl-3-phenylpropanoate

Participants

Reaction Steps

Dissolved LiAl(OtBu)3H (509 mg, 2.0 mmol) in 2 mL THF and then added a solution of dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)-2-methylmalonate (215 mg, 0.48 mmol) in 2 mL of THF. After 12 h, the reaction was incomplete so more LiAl(OtBu)3H (509 mg, 2.0 mmol) was added. After 12 h, quenched with MeOH, poured into brine and extracted with EtOAc×3. The organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified on SiO2 by MPLC using a 1:3 to 1:1 EtOAc/hexane gradient. Obtained 121 mg (60% yield) of methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-(hydroxymethyl)-2-methyl-3-phenylpropanoate. MS found: (M+H)+=419.

Provenance & Evidence