HCID 21968280, compound → HCID 21968279, compound

HRID 1106508Notes

Reaction equation

HRID 1106508 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[NH:8][C@@H:7]3[CH2:12][CH2:13][N:14](CC4C=CC=CC=4)[CH2:15][C@H:6]3[C:5]=2[CH:4]=1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[NH:8][C@@H:7]3[CH2:12][CH2:13][NH:14][CH2:15][C@H:6]3[C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 21968280HCID 21968280, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21968279HCID 21968279, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate 8 (11.3 g) in methanol (250 ml) was hydrogenated with palladium-on-carbon (10%, 2 g) as a catalyst. After uptake of hydrogen (1 equivalent), the catalyst was filtered off and the filtrate was evaporated. The residue was solidified in DIPE (30 ml). The precipitate was filtered off and dried, yielding 6.1 g (78%) of (±)-trans-2,3,4,4a,5,9b-hexahydro-8-methoxy-1H-pyrido[4,3-b]indole (intermediate 10).

Workup

  1. customthe filtrate was evaporated
  2. filtrationThe precipitate was filtered off
  3. customdried

Sources & evidence

ORD record
ord-101d16f8f0d4451f89cd84ce1543db2d
Source dataset
uspto-grants-2000_05
Patent number
US06057325

Reaction notes

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