5-Methoxytryptamine → Tetrahydro-beta-carboline

Participants

Reaction Conditions

Reaction Steps

5-Methoxy tryptamine 1a or 6-methoxy tryptamine 1b (0.524 mmol) and appropriate aryl or heteroaryl aldehyde 2 (0.63 mmol) were dissolved in THF (20 mL). The reaction mixture was cooled to 0° C. CF3COOH (0.2 ml) was then added at 0° C., and the reaction mixture was then allowed to stir at 0° C. for 1 hr. The ice bath was then removed and the reaction allowed to stir for a further 1 hr from 0° C. to r.t. The reaction mixture was quenched with aqueous saturated NaHCO3 (5 ml) and the organic phase separated. The mixture was extracted with EtOAc (2×10 ml). The combined organic phase was dried (anhydrous NaSO4), filtered and evaporated in vacuo to give the crude product tetrahydro β-carboline 3. The crude product was directly used for second step with out further purification.

Provenance & Evidence