HCID 69663704, compound → HCID 58618739, compound

HRID 1794225Notes

Reaction equation

HRID 1794225 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[O:11][C:10]2[CH:12]=[CH:13][C:14]([CH2:16][CH2:17][NH:18][CH2:19][C@H:20]([OH:39])[CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([O:29]CC4C=CC=CC=4)=[CH:25][C:24]=3[O:37][CH3:38])=[CH:15][C:9]=2[O:8][CH2:7]1)=[O:5])[CH3:2]>C(O)C.[C].[Pd]>[CH2:1]([O:3][C:4]([C@@H:6]1[O:11][C:10]2[CH:12]=[CH:13][C:14]([CH2:16][CH2:17][NH:18][CH2:19][C@H:20]([OH:39])[CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=3[O:37][CH3:38])=[CH:15][C:9]=2[O:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 69663704HCID 69663704, compound

Product 1

HCID 58618739HCID 58618739, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 6-[2-[3-(4-benzyloxy-2-methoxyphenoxy)-2-(S)-hydroxypropylamino]ethyl]-2,3-dihydro-1,4-benzodioxine-2-(R)-carboxylic acid ethyl ester obtained in Example 17 (240 mg) in ethanol (10 mL) was added 10% palladium-carbon (24 mg). This solution was stirred under hydrogen atmosphere at room temperature for 6 hours. After filtration through Celite, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel and the title compound (129 mg) was obtained from the effluent with chloroform/methanol/aqueous ammonia=85/15/0.1 (v/v). Yield: 64%

Workup

  1. filtrationAfter filtration through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8c40ac21558345b8b41043ca12d46db6
Source dataset
uspto-grants-2006_04
Patent number
US07022732B2

Reaction notes

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