Aluminium lithium hydride → HCID 58986338, compound

Participants

Reaction Conditions

Reaction Steps

To −78° C. solution of 1-benzyl-2-isopropyl-5-(tetrahydropyran-2-yloxy)-1H-indole-3-carboxylic acid, ethyl ester (Compound 11, 2.11 g, 5 mmol) in THF (30 mL) was added a 1 M solution of LiAlH4 in THF (9 mL, 9 mmol) dropwise over 5 minutes. The mixture was gradually warmed to 0° C. over 4 h. The reaction was cooled to −78° C. and quenched by adding EtOAc (5 mL) and saturated aqueous Na2SO4 (9 mL). The solution was warmed to room temperature and stirred for 20 minutes. The resulting precipitate was filtered off, and the organic layer was dried (Na2SO4). The solvent was removed under vacuum to obtain (1-benzyl-2-isopropyl-5-(tetrahydropyran-2-yloxy)-1H-indol-3-yl)methanol (Compound 12) as a white solid.

Provenance & Evidence