A 30312 → HCID 21968280, compound

HRID 1106507Notes

Reaction equation

HRID 1106507 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C:8]3[CH2:13][CH2:14][N:15]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:16][C:7]=3[C:6]=2[CH:5]=1.[BH4-].[Na+]>COCCOCCOC>[CH3:2][O:3][C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C@@H:8]3[CH2:13][CH2:14][N:15]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:16][C@H:7]3[C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 132598A 30312HCID 4311764Sodium borohydride

Product 1

HCID 21968280HCID 21968280, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A mixture of 2,3,4,5-tetrahydro-8-methoxy-2-(phenylmethyl)-1H-pyrido[4,3-b]indole monohydrochloride (39.5 g), prepared as described in J. Org. Chem. 44:1063-1068 (1979), in 2-methoxyethyl ether (250 ml) was stirred and cooled in an ice bath, under a N2 flow. Sodium borohydride (11.7 g, solid) was added in 8 portions. The mixture was stirred overnight at room temperature, then cooled to 5° C. Ice water (500 ml) was added dropwise. Precipitation resulted. The mixture was stirred for 2 hours. The precipitate was filtered off. 1,4-Dioxane (350 ml) was added and the mixture was stirred. HCl (200 ml, 12N) was slowly added and the mixture was heated to reflux temperature. The mixture was stirred and refluxed for 1 hour, then cooled and the solvent was evaporated. The residue was stirred in water (300 ml) and this mixture was alkalized with an aqueous NaOH solution. The mixture was stirred for 1 hour. The mixture was extracted with DCM (2×200 ml). The combined extracts were dried, filtered and the solvent was evaporated. The residue was dissolved in DIPE (300 ml), then filtered and the filtrate was evaporated, yielding 11.3 g (32%) of (±)-trans-2,3,4,4a,5,9b-hexahydro-8-methoxy-2-(phenylmethyl)-1H-pyrido[4,3-b]indole (intermediate 8).

Workup

  1. customprepared
  2. temperaturecooled in an ice bath, under a N2 flow
  3. temperaturecooled to 5° C
  4. customPrecipitation
  5. customresulted
  6. stirringThe mixture was stirred for 2 hours
  7. filtrationThe precipitate was filtered off
  8. addition1,4-Dioxane (350 ml) was added
  9. stirringthe mixture was stirred
  10. additionHCl (200 ml, 12N) was slowly added
  11. temperaturethe mixture was heated
  12. temperatureto reflux temperature
  13. stirringThe mixture was stirred
  14. temperaturerefluxed for 1 hour
  15. temperaturecooled
  16. customthe solvent was evaporated
  17. stirringThe residue was stirred in water (300 ml)
  18. stirringThe mixture was stirred for 1 hour
  19. extractionThe mixture was extracted with DCM (2×200 ml)
  20. customThe combined extracts were dried
  21. filtrationfiltered
  22. customthe solvent was evaporated
  23. dissolutionThe residue was dissolved in DIPE (300 ml)
  24. filtrationfiltered
  25. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-4a4a32db091843d19371ae27c28acf48
Source dataset
uspto-grants-2000_05
Patent number
US06057325

Reaction notes

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