HCID 53891592, compound → HCID 19966230, compound

HRID 977819Notes

Reaction equation

HRID 977819 reaction equation
[OH:1][CH:2]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12][CH3:13])[C:6]=1[NH:14][C:15](=[O:31])[CH2:16][CH:17]1[C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:24][C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2.[H][H]>[Pd].O1CCCC1>[OH:1][CH:2]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12][CH3:13])[C:6]=1[NH:14][C:15](=[O:31])[CH2:16][CH:17]1[C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:24][C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2

Participants

5

Reactant 2

HCID 53891592HCID 53891592, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19966230HCID 19966230, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

35 mg of 10% w/w palladium-on-carbon were added to 15 ml of a tetrahydrofuran solution containing 111 mg (0.226 mmol) of N-[2-(3-hydroxy-3-phenyl-1-propenyl)-6-methoxymethylphenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Example 6), and the mixture was stirred vigorously for 15 hours in a stream of hydrogen. The reaction solution was then filtered with the help of a Celite (trade mark) filter aid, and the catalyst was washed with tetrahydrofuran. The filtrate and the washings were combined, and the solvent was removed from the combined solution by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 15 g of silica gel. Elution with a 4:1 by volume mixture of methylene chloride and ethyl acetate afforded 86 mg (yield 77%) of the title compound as crystals, melting at 143.5°-146° C. (after recrystallization from a mixture of methanol and hexane).

Workup

  1. filtrationThe reaction solution was then filtered with the help of a Celite (trade mark)
  2. filtrationfilter aid
  3. washthe catalyst was washed with tetrahydrofuran
  4. customthe solvent was removed from the combined solution by distillation under reduced pressure
  5. washElution with a 4:1
  6. additionby volume mixture of methylene chloride and ethyl acetate

Sources & evidence

ORD record
ord-dacb13a031514f37b079229d16451215
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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