HCID 86670448, compound → HCID 86670449, compound

HRID 1972698Notes

Reaction equation

HRID 1972698 reaction equation
C([O:8][CH2:9][C@@H:10]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)[CH2:14][CH2:13][N:12]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:11]1)C1C=CC=CC=1>[Pd].CCO>[OH:8][CH2:9][C@@H:10]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([OH:31])([C:23]([F:24])([F:25])[F:26])[C:27]([F:28])([F:29])[F:30])=[CH:18][CH:17]=2)[CH2:14][CH2:13][N:12]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:11]1

Participants

4

Reactant 1

HCID 86670448HCID 86670448, compound

Product 1

HCID 86670449HCID 86670449, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 150-mL round-bottomed flask was charged with tert-butyl (3R)-3-((benzyloxy)methyl)-4-(4-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)phenyl)-1-piperazinecarboxylate (0.917 g, 1.67 mmol), palladium on activated carbon (10 wt %, wet, degussa type, 1.34 g, 0.632 mmol, Sigma-Aldrich, St. Louis, Mo.) and EtOH (15 mL). The reaction mixture was evacuated under vacuum and refilled with hydrogen (5 times). The mixture was hydrogenated under balloon pressure of hydrogen at 60° C. for 2 h. The catalyst was removed via filtration through a pad of filter agent. The filter cake was covered with sand and washed with EtOH. The filtrate was concentrated to give tert-butyl (3R)-3-(hydroxymethyl)-4-(4-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)phenyl)-1-piperazinecarboxylate (0.767 g) as a white solid.

Workup

  1. customThe reaction mixture was evacuated under vacuum
  2. additionrefilled with hydrogen (5 times)
  3. customThe catalyst was removed via filtration through a pad of filter agent
  4. washwashed with EtOH
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-86b4ca175d1946899ea2711edb1f66f9
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

Loading…