Sodium bis(2-methoxyethoxy)aluminiumhydride → HCID 70390354, compound

Participants

Reaction Steps

To a 500 ml round bottomed flask with stirring bar, reflux condenser, dropping funnel and argon inlet was added a solution of sodium bis (2-methoxyethoxy)aluminum hydride (20.63 ml of a 3.4 M solution in toluene) and 100 ml of dry THF. This solution was heated at reflux and a solution of the acetamide (5.04 g, 17.54 mmol) from Step B in 100 ml of dry THF was added dropwise over 45 minutes. When the addition was complete the mixture was heated at reflux for 2 hours. The reaction mixture was chilled in an ice bath and quenched with 100 ml of saturated aqueous potassium sodium tartrate solution. The resulting mixture was diluted with ethyl acetate (300 ml) and the layers were separated. The organic phase was washed with an additional 200 ml of tartrate solution and 200 ml of brine. Drying (K2CO3), filtration and removal of the solvent in vacuo left 4.90 g of (2RS, 11bSR)-2-methylamino-2-(2 -methylaminoethyl)-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine as an oil.

Provenance & Evidence