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

To a 500 ml round bottomed flask with stirring bar, refluxed condenser, dropping funnel and argon inlet was added a solution of sodium bis (2-methoxyethoxy)aluminum hydride (20.63 ml of a 3.4M 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.

1. temperaturerefluxed condenser
2. temperatureThis solution was heated
3. temperatureat reflux
4. additionWhen the addition
5. temperaturewas heated
6. temperatureat reflux for 2 hours
7. temperatureThe reaction mixture was chilled in an ice bath
8. customquenched with 100 ml of saturated aqueous potassium sodium tartrate solution
9. additionThe resulting mixture was diluted with ethyl acetate (300 ml)
10. customthe layers were separated
11. washThe organic phase was washed with an additional 200 ml of tartrate solution and 200 ml of brine
12. customDrying
13. filtration(K2CO3), filtration and removal of the solvent in vacuo
14. waitleft 4.90 g of (2RS,11bSR)-2-methylamino-2-(2-methylaminoethyl)- 1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine as an oil

ORD record

ord-40ca940f1927487ba5ec03296ae6b9e1

Source dataset

uspto-grants-1989_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04824849