Aluminium lithium hydride → (R)-2-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutan-1-ol

Participants

Reaction Steps

To a stirred suspension of LiAlH4 (40 mg, 1 mmol) in anhydrous THF (2 mL) under N2 at −78° C. was added dropwise a solution of (R)-2-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutanoic acid (150 mg, 0.5 mmol) in anhydrous THF (1 mL). The mixture was allowed to warm to rt and stirred for 24 h. TLC showed the starting material had been consumed. The mixture was cooled to 0° C., H2O (40 uL) was added dropwise, followed by 10% aq NaOH (40 uL). The mixture was filtered and the filtrate was evaporated. The residue was partitioned between EtOAc and water, and extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to give (R)-2-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutan-1-ol (115 mg, 79%). 1H NMR (400 MHz, CDCl3): 1.00 (m, 6H), 1.72 (m, 3H), 2.16 (m, 2H), 2.68 (m, 1H), 2.88 (m, 1H), 3.27 (m, 2H), 3.29 (s, 3H), 3.58 (m, 2H), 4.48 (m, 2H), 7.00 (m, 1H), 7.23 (m, 1H), 7.62 (m, 1H), 7.96 (m, 1H); MS: 291 (M++1)

Provenance & Evidence