HCID 67483413, compound → HCID 135819148, compound

HRID 324869Notes

Reaction equation

HRID 324869 reaction equation
[CH:1]([C:4]1[C:9]([CH:10]([OH:12])[CH3:11])=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19]CC2C=CC=CC=2)[C:7]([CH:27]=[CH:28][CH2:29][CH2:30][CH3:31])=[C:6]([CH:32]([CH3:34])[CH3:33])[N:5]=1)([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:1]([C:4]1[C:9]([CH:10]([OH:12])[CH3:11])=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[C:7]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:6]([CH:32]([CH3:33])[CH3:34])[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67483413HCID 67483413, compound

Product 1

HCID 135819148HCID 135819148, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The diastereomeric mixture of intermediates from Step B (39 mg) was dissolved in absolute ethanol (1.5 mL) under argon, treated with 10% palladium on carbon (4 mg), then stirred under a hydrogen atmosphere for 8 hr. After purging the system with argon, the catalyst was removed by filtration through a pad of Celite. The solvent was removed and the product dried in vacuo to afford 32 mg of the title compound as a colorless solid. Preparative thin layer chromatography (“prep TLC”) using a 20% ethyl acetate-hexane mixture as the eluent provided the two diastereomers.

Workup

  1. customAfter purging the system with argon
  2. customthe catalyst was removed by filtration through a pad of Celite
  3. customThe solvent was removed
  4. customthe product dried in vacuo

Sources & evidence

ORD record
ord-b54127e825574e6497db5340b07d19cb
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

Loading…