Aluminium lithium hydride → HCID 44292367, compound

Participants

Reaction Steps

A solution of LAH (39 mL, 1 M in THF, 39 mmol) was added slowly to a cooled (0° C.) solution of (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-5-methyl-1H-indole (Example 1b, 9.5 mmol) in THF (100 mL). Once the addition was completed, the reaction mixture was stirred at reflux overnight prior to quenching with sodium sulfate decahydrate. The product was taken into ethyl acetate, filtered to remove the solid residue, and the solvent was removed in vacuo. The product was taken into ethyl acetate, filtered to remove the solid residue, and the solvent was removed in vacuo. Flash chromatography (silica gel, 6% 2M methanolic ammonia in dichloromethane) yielded (R)-5-methyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indole (52%; yellow oil; HRMS-FAB+ for C15H20N2 : calculated MH+ :229.1705; found MH+ :229.1706).

Provenance & Evidence