1,4-Dioxane hydrochloride → HCID 57666083, compound

HRID 889691Notes

Reaction equation

HRID 889691 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH:5]([C:10]1[CH:11]=[C:12]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].Cl.O1CCOCC1>CO.[Pt]=O>[CH2:1]([O:3][C:4](=[O:33])[CH:5]([C:10]1[CH:11]=[C:12]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH:18]([CH3:22])[NH:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 57665989HCID 57665989, compound

Product 1

HCID 57666083HCID 57666083, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A solution of 4-Methyl-2-[5-(6-methyl-pyridin-2-yl)-4′-trifluoromethyl-biphenyl-3-yl]-pentanoic acid ethyl ester, compound 6b (161 mg, 0.35 mmol) in MeOH (12 mL), platinum oxide (8.0 mg, 0.35 mmol) and 4N HCl/dioxane (97.3 μL) was hydrogenated at 40 psi for 6 hours. The reaction mixture was filtered through celite, washed with MeOH and concentrated in vacuo. The residue was partitioned between dichloromethane/Na2CO3 and extracted 3×, dried over MgSO4, filtered and concentrated to give the product as a pink oil (202 mg, quant.) (M+H) 461.56, Found 462.3.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with MeOH
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between dichloromethane/Na2CO3
  5. extractionextracted 3×
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e18ffee18ebc42fe802310fe8b0d0632
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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