HCID 58986346, compound → HCID 66658608, compound

Participants

Reaction Steps

General Procedure C. To a −78° C. solution of (1-benzyl-2-isopropyl-5-(tetrahydropyran-2-yloxy)-1H-indole-3-carboxaldehyde (Compound 13, 200 mg, 0.55 mmol) in THF (5 mL) was added MeMgBr (3 M solution in THF, 1 mL, 3 mmol). The solution was stirred between −78° C. and −10° C. for 4 h, and then the reaction was quenched at −78° C. by adding EtOAc (2 mL) and water (5 mL). The mixture was warmed to room temperature and diluted with EtOAc (50 mL). The reaction was quickly washed with ice cold aqueous NH4Cl (5 mL), and brine (10 mL), and dried (Na2SO4), and the solvent was removed under vacuum to give 1-(1-benzyl-2-isopropyl-5-(tetrahydropyran-2-yloxy)-1H-indol-3-yl)ethanol as a mixture of two diastereomers that were used directly in the next step without further purification or characterization. Thus, crude 1-(1-benzyl-2-isopropyl-5-(tetrahydropyran-2-yloxy)-1H-indol-3-yl)ethanol (200 mg, 0.51 mmol) was oxidized to 1-(1-benzyl-2-isopropyl-5-(tetrahydropyran-2-yloxy)-1H-indol-3-yl)ethanone (Compound 14) by General Procedure B.

Provenance & Evidence