6-methoxy-1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline synthesis
- Product Name:6-methoxy-1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline
- CAS Number:5684-66-2
- Molecular formula:C18H18N2O
- Molecular Weight:278.35
Yield:5684-66-2 82%
Reaction Conditions:
with 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide in ethyl acetate at 110; for 0.166667 h;Microwave irradiation;Sealed tube;
Steps:
General experimental procedure for compounds 3a, 3c-3h, 3j, 3q and 3r
General procedure: T3P (50% in EtOAc) (2.5 equiv, 1.25 mmol) was added to a mixture of tryptamine (1a, 0.5 mmol) and benzaldehyde (2a, 0.5 mmol) in a microwave vial. The reaction volume was then adjusted to 0.5 mL with EtOAc and the vessel was sealed. The mixture was heated under microwave irradiation (Biotage Initiator) at 110 °C for 10 min. The residue was diluted with EtOAc and washed successively with a saturated solution of NaHCO3 (2 × 5 mL) and brine (5 mL). The organic layer was dried over Na2SO4. Evaporation of the solvent afforded the expected product in sufficient purity.
References:
Desroses, Matthieu;Koolmeister, Tobias;Jacques, Sylvain;Llona-Minguez, Sabin;Jacques-Cordonnier, Marie-Caroline;Cázares-K?rner, Armando;Helleday, Thomas;Scobie, Martin [Tetrahedron Letters,2013,vol. 54,# 27,p. 3554 - 3557] Location in patent:supporting information
