HCID 68558838, compound → HCID 58972243, compound

HRID 20384Notes

Reaction equation

HRID 20384 reaction equation
C([N:8](CC1C=CC=CC=1)[C@@H:9]([CH2:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[C:35]([F:40])[CH:34]=1)[C@H:10]([O:24]CC1C=CC=CC=1)[C@H:11]1[CH2:16][O:15][C@@H:14]([O:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C@H:13]([CH3:23])[NH:12]1)C1C=CC=CC=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:8][C@@H:9]([CH2:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[C:35]([F:40])[CH:34]=1)[C@@H:10]([C@H:11]1[CH2:16][O:15][C@@H:14]([O:17][CH2:18][C:19]([CH3:21])([CH3:22])[CH3:20])[C@H:13]([CH3:23])[NH:12]1)[OH:24]

Participants

5

Reactant 2

HCID 68558838HCID 68558838, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58972243HCID 58972243, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Add 20% palladium hydroxide on carbon (679 mg) to a solution of dibenzyl-{(1S,2R)-2-benzyloxy-1-(3,5-difluorobenzyl)-2-[(3R,5S,6R)-6-(2,2-dimethylpropoxy)-5-methylmorpholin-3-yl]-ethyl}-amine (284 mg, 0.442 mmol) in absolute ethanol (5 mL) and stir under 1 atmosphere of hydrogen gas at room temperature for 18 hours. Filter through a pad of Celite®, wash thoroughly with ethanol and concentrate to give the desired compound as a glass (162 mg, 98%).

Workup

  1. filtrationFilter through a pad of Celite®
  2. washwash thoroughly with ethanol
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-36db04c3dcb9420e8a136e9c40e0de93
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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