HCID 11727809, compound → HCID 22004794, compound

HRID 324645Notes

Reaction equation

HRID 324645 reaction equation
[Br:1][C:2]1[C:11]2[O:10][CH2:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH:12]([CH2:15][CH2:16][NH:17][C:18](=[O:21])[CH2:19][CH3:20])[CH2:13][CH2:14][C:4]=2[CH:3]=1>C(O)C.[Pd]>[Br:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]2[CH:12]([CH2:15][CH2:16][NH:17][C:18](=[O:21])[CH2:19][CH3:20])[CH2:13][CH2:14][C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 11727809HCID 11727809, compound

Product 1

HCID 22004794HCID 22004794, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-[2-(5-bromo-3,7,8,9-tetrahydrocyclopenta[f][1]benzopyran-9-yl)ethyl]propionamide (1.2 g, 3.4 mmol.) in ethanol (10 mL) was added 5% Pd-C (120 mg, 50% hydrous). The mixture was stirred for one hour at room temperature under hydrogen atmosphere. The reaction mixture was subjected to filtration. The filtrate was concentrated under reduced pressure. The concentrate was purified by means of silica gel column chromatography (ethyl acetate) to afford the title compound (yield 327 mg, 27%).

Workup

  1. filtrationThe reaction mixture was subjected to filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe concentrate was purified by means of silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-db2bd715bf3845af948a33f2ad5838f6
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

Loading…