HCID 66680048, compound → HCID 66679053, compound

HRID 1629588Notes

Reaction equation

HRID 1629588 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C([O:13][CH2:14][CH2:15][N:16]1[C:28]2[CH2:27][CH2:26][CH2:25][CH:24]([C:29]([OH:31])=[O:30])[C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][C:21]=2[O:32][CH3:33])C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[OH:13][CH2:14][CH2:15][N:16]1[C:28]2[CH2:27][CH2:26][CH2:25][CH:24]([C:29]([OH:31])=[O:30])[C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][C:21]=2[O:32][CH3:33]

Participants

5

Reactant 2

HCID 66680048HCID 66680048, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66679053HCID 66679053, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

9-(2-Benzyloxy-ethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamine (10) (1.0 g, 2.1 mmol) in methanol (50 ml) was shaken with 10% palladium on charcoal (300 mg), and hydrogen gas excess for 18 h at 55° C. The reaction was then filtered through a pad of celite and the filtrate concentrated in vacuo to give 578 mg (100%) 9-(2-hydroxyethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamine (11) as a foam. The structure was confirmed by 13C NMR (75 MHz; CDCl3): δC 13.0, 14.4, 20.0, 22.0, 28.0, 36.4, 40.6, 42.0, 54.7, 60.6, 99.2, 1026, 107.0, 116.7, 121.1, 136.1, 137.5, 138.0 153.5, and 175.7.

Workup

  1. filtrationThe reaction was then filtered through a pad of celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-1ad4f47bf5ae46198933f03db233e159
Source dataset
uspto-grants-2014_07
Patent number
US08790619B2

Reaction notes

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