6-benzyloxy-3-methyl-2,3,4,9-tetrahydro-1H-beta-carboline → HCID 22018508, compound

HRID 6752Notes

Reaction equation

HRID 6752 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH2:16][NH:15][CH:14]([CH3:22])[CH2:13][C:12]2=1)C1C=CC=CC=1>C(O)C.[Pd]>[CH3:22][CH:14]1[CH2:13][C:12]2[C:11]3[C:19](=[CH:20][CH:21]=[C:9]([OH:8])[CH:10]=3)[NH:18][C:17]=2[CH2:16][NH:15]1

Participants

4

Reactant 1

HCID 220185146-benzyloxy-3-methyl-2,3,4,9-tetrahydro-1H-beta-carboline

Product 1

HCID 22018508HCID 22018508, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 6-benzyloxy-3-methyl-2,3,4,9-tetrahydro-1H-β-carboline (60 mg) in ethanol (4 mL) was added to a suspension of 10% Pd/C (100 mg) in ethanol (10 mL). The mixture was stirred at rt for 16 h under an atmosphere of hydrogen. The mixture was filtered through celite and evaporation of the filtrate yielded 3-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-6-ol (30 mg).

Workup

  1. filtrationThe mixture was filtered through celite and evaporation of the filtrate

Sources & evidence

ORD record
ord-6e073a3a3c75488e81aeb22ebd875f71
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Reaction notes

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