Reaction #437978

Reaction equation

o-xylene

1-octene

tert-butyl (6bR,10aS)-5-(2,4-dichlorophenyl)-3-methyl-2-oxo-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate

BH3-THF

→

tert-butyl (6bR,10aS)-5-(2,4-dichlorophenyl)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate

Yield 58.0%

Solvents

THF

Conditions

Workup

1. 1
   workup.ADDITIONAfter addition
2. 2
   Otherthe resulting reaction mixture
3. 3
   Temperaturewas refluxed for 4 h
4. 4
   Otherquenched cautiously with water (1.0 mL)
5. 5
   OtherThe mixture was evaporated to dryness under reduced pressure
6. 6
   Otherthe residue obtained
7. 7
   Temperatureheated
8. 8
   Temperatureat reflux for 4 h
9. 9
   TemperatureThe reaction mixture was cooled to room temperature
10. 10
    Concentrationconcentrated to dryness under reduced pressure

Procedure

To a solution of tert-butyl (6bR,10aS)-5-(2,4-dichlorophenyl)-3-methyl-2-oxo-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (100 mg, 0.21 mmol) in THF (5.0 mL), BH3-THF (1M in THF) (0.82 mL, 0.82 mmol) was added dropwise. After addition was completed, the resulting reaction mixture was refluxed for 4 h, cooled to room temperature, and quenched cautiously with water (1.0 mL). The mixture was evaporated to dryness under reduced pressure and the residue obtained was treated with o-xylene (10 mL) and 1-octene (5 mL) and heated at reflux for 4 h. The reaction mixture was cooled to room temperature and concentrated to dryness under reduced pressure to give tert-butyl (6bR,10aS)-5-(2,4-dichlorophenyl)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate as a white solid (50 mg, 58%).

Source