HCID 67289265, compound → HCID 67292031, compound

HRID 511859Notes

Reaction equation

HRID 511859 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:15]([NH:17][C:18](=[O:31])[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH3:16])=[N:13][CH:14]=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:15]([NH:17][C:18](=[O:31])[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:23][CH:22]=2)[CH3:16])=[N:13][CH:14]=1

Participants

4

Reactant 1

HCID 67289265HCID 67289265, compound

Product 1

HCID 67292031HCID 67292031, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R)-N-(1-(5-(benzyloxy)pyridin-2-yl)ethyl)-2-(4-(trifluoromethyl)phenoxy)acetamide (Example 63, 550 mg, 1.3 mmol) and palladium hydroxide on carbon (20 wt. %, 50 mg) in methanol (30 mL) was hydrogenated for 6 hours. The mixture was filtered through a pad of celite, washed with methanol, the filtrate was concentrated gave 410 mg (94% yield) of (R)-N-(1-(5-hydroxypyridin-2-yl)ethyl)-2-(4-(trifluoromethyl)phenoxy)acetamide as a white crystalline solid;

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a4a596a516e54b3f8e1393f9e2766747
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

Loading…