HCID 178438828, compound → HCID 178438827, compound

HRID 1422855Notes

Reaction equation

HRID 1422855 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([CH:23]([CH3:25])[CH3:24])=[CH:11][C:10]=1[C:26]1[N:27]([C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[CH2:37][C:36]2([O:44][CH2:43][CH2:42][O:41]2)[CH2:35]3)[C:28]([OH:31])=[N:29][N:30]=1)C1C=CC=CC=1>CCOC(C)=O.CCCCCC.[Pd]>[CH2:37]1[C:38]2[C:34](=[CH:33][C:32]([N:27]3[C:28]([OH:31])=[N:29][N:30]=[C:26]3[C:10]3[CH:11]=[C:12]([CH:23]([CH3:25])[CH3:24])[C:13]([OH:15])=[CH:14][C:9]=3[OH:8])=[CH:40][CH:39]=2)[CH2:35][C:36]21[O:41][CH2:42][CH2:43][O:44]2

Participants

4

Reactant 1

HCID 178438828HCID 178438828, compound

Product 1

HCID 178438827HCID 178438827, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

5-(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-4-(1′,3′-dihydro-spiro[[1,3]dioxolane-2,2′-inden]-5′-yl)-4H-[1,2,4]triazol-3-ol (550 mg, 0.93 mmol) was subsequently hydrodebensylated using Pd/C (10%, dry, 100 mg) and H2 in THF/MeOH (1/1, 25 mL) at 1 atm at r.t. for 2 h. The reaction mixture was filtered through a pad of celite and the mother liquid was concentrated. It was again filtered through a pad of silica gel and the filtrate was concentrated to give the title compound as a white solid (370 mg, 97%).

Workup

  1. customat r.t.
  2. customfor 2 h
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. concentrationthe mother liquid was concentrated
  5. filtrationIt was again filtered through a pad of silica gel
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9c430ad8e4b14d02833f1f41854252f2
Source dataset
uspto-grants-2015_01
Patent number
US08927548B2

Reaction notes

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