HCID 11727809, compound → HCID 22004794, compound

HRID 1636619Notes

Reaction equation

HRID 1636619 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-fa60be3db33c46a6bbd77f25f9465e23
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

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