HCID 22004846, compound → HCID 22004849, compound

HRID 1636620Notes

Reaction equation

HRID 1636620 reaction equation
Br[CH:2]1[C:11]2[O:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]2[C:12]([CH2:15][CH2:16][NH:17][C:18](=[O:21])[CH2:19][CH3:20])=[CH:13][CH2:14][C:4]=2[CH2:3]1>C(O)C.[Pd]>[CH2:7]1[C:6]2[C:5]3[C:12]([CH2:15][CH2:16][NH:17][C:18](=[O:21])[CH2:19][CH3:20])=[CH:13][CH2:14][C:4]=3[CH2:3][CH2:2][C:11]=2[O:10][CH2:9][CH2:8]1

Participants

4

Reactant 1

HCID 22004846HCID 22004846, compound

Product 1

HCID 22004849HCID 22004849, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-[2-(5-bromo-2,3,4,5,6,7-hexahydrocyclopenta[f][1]benzopyran-9-yl)ethyl]propionamide (200 mg, 0.6 mmol.) in ethanol (5 mL) was added 5% Pd-C (200 mg, 50% hydrous). The mixture was stirred for 3 hours at room temperature under hydrogen atmosphere. The reaction mixture was subjected to filtration. The filtrate was then concentrated under reduced pressure. The concentrate was purified by means of silica gel column chromatography to afford the title compound (yield 130 mg, 85%).

Workup

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

Sources & evidence

ORD record
ord-ab0be2ad04cf4adaa11af0e4e8852d87
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

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