1,4-Dioxane hydrochloride → 4-Methyl-2-(5-piperidin-2-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

HRID 889702Notes

Reaction equation

HRID 889702 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][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:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][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 576660264-Methyl-2-(5-pyridin-2-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 576660784-Methyl-2-(5-piperidin-2-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A solution of 4-Methyl-2-(5-pyridin-2-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester, compound 10a (30 mg, 0.068 mmol) in MeOH (2.3 mL), platinum oxide (1.55 mg, 0.007 mmol) and 4N HCl/dioxane (19 μl) was hydrogenated at 30 psi for 3 hours. The reaction mixture was filtered through celite, washed with MeOH and concentrated in vacuo. The residue was partitioned between dichloromethane and Na2CO3 to give the free base; (30 mg, 99%). Calculated for C26H32F3NO2 (M+H) 447.53, Found 448.4

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with MeOH
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between dichloromethane and Na2CO3
  5. customto give the free base

Sources & evidence

ORD record
ord-1e53154ee5fa42b9a6df3f9758d38fa3
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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