HCID 50993082, compound → Abediterol

HRID 39346Notes

Reaction equation

HRID 39346 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:40])[CH2:21][NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]([F:39])([F:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1>CO.[Pd]>[F:39][C:31]([F:38])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:30][O:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][NH:22][CH2:21][C@@H:20]([C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:19])[NH:17]2)[OH:40]

Participants

4

Reactant 1

HCID 50993082HCID 50993082, compound

Product 1

HCID 11962616AbediterolYield 54.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To Intermediate (II) (1.10 g, 2.0 mmol) in methanol (50 mL) was added 20% palladium on charcoal (300 mg). The mixture was hydrogenated at 2 bars for 3 hours. The catalyst was filtered through Celite and the solvent concentrated. The resulting oil was purified by column chromatography with silica gel eluting with methylene chloride/methanol (95:5) to give the title compound (0.50 g, 54%) as oil.

Workup

  1. filtrationThe catalyst was filtered through Celite
  2. concentrationthe solvent concentrated
  3. customThe resulting oil was purified by column chromatography with silica gel eluting with methylene chloride/methanol (95:5)

Sources & evidence

ORD record
ord-f7a3216fab9c45d9aeb0c89f487194fa
Source dataset
uspto-grants-2013_09
Patent number
US08524908B2

Reaction notes

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