Ethyl 1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate → HCID 44593836, compound

HRID 1106505Notes

Reaction equation

HRID 1106505 reaction equation
[CH2:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH2:4][CH2:3][N:2]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>N.CO.[Ni]>[CH2:1]1[C@H:13]2[C@H:5]([NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=32)[CH2:4][CH2:3][N:2]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 1

HCID 1756750Ethyl 1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Product 1

HCID 44593836HCID 44593836, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of ethyl 1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (49.2 g), prepared as described in J. Med. Chem. 23:635-643 (1980), in NH3 /CH3OH (400 ml) was hydrogenated with Raney nickel (5 g) as a catalyst. The mixture was cooled and the catalyst was filtered off. The filtrate was evaporated. The residue was dissolved in anhydrous diethyl ether (600 ml) and HCl(g) was allowed to bubble through the solution for 30 minutes. The resulting precipitate was filtered off, dissolved in water (200 ml) and extracted with diethyl ether (100 ml). The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was solidified in DIPE (150 ml), cooled to 0° C., filtered off and dried, yielding 34.3 g (70%) of (±)-ethyl cis-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate (intermediate 1).

Workup

  1. customprepared
  2. temperatureThe mixture was cooled
  3. filtrationthe catalyst was filtered off
  4. customThe filtrate was evaporated
  5. dissolutionThe residue was dissolved in anhydrous diethyl ether (600 ml)
  6. customto bubble through the solution for 30 minutes
  7. filtrationThe resulting precipitate was filtered off
  8. dissolutiondissolved in water (200 ml)
  9. extractionextracted with diethyl ether (100 ml)
  10. customThe organic layer was separated
  11. customdried
  12. filtrationfiltered
  13. customthe solvent was evaporated
  14. filtrationfiltered off
  15. customdried

Sources & evidence

ORD record
ord-520dd68f457f493c9cde9e484175ea23
Source dataset
uspto-grants-2000_05
Patent number
US06057325

Reaction notes

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