Hydrochloric Acid → 2-(ethyloxy)-N-((1RS,2RS)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-1-naphthalenecarboxamide

HRID 1610179Notes

Reaction equation

HRID 1610179 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:14]([NH:16][CH:17]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=1)[C:18]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=[O:19])=[O:15])[CH3:2].[BH4-].[Na+].Cl>CO.[Cl-].[Mn+2].[Cl-]>[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:14]([NH:16][CH:17]([CH2:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]([F:37])([F:35])[F:36])=[CH:32][CH:33]=1)[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[OH:19])=[O:15])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 222620222-(ethyloxy)-N-(2-(4-fluorophenyl)-2-oxo-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-1-naphthalenecarboxamide

Product 1

HCID 222620302-(ethyloxy)-N-((1RS,2RS)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-1-naphthalenecarboxamideYield 57%

Reagents, catalysts & solvents 2

HCID 10313134Manganese(2+) dichlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(ethyloxy)-N-(2-(4-fluorophenyl)-2-oxo-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-1-naphthalenecarboxamide (400 mg, 0.79 mmol) in methanol (30 ml) was added manganese (II) chloride (198 mg, 1.57 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction solution was added sodium borohydride (30 mg, 0.79 mmol) under ice-cooling, and the mixture was stirred for 1 hr. The reaction solution was poured into 1N hydrochloric acid (30 ml), and extracted with ethyl acetate (50 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-1:1 and recrystallized from ethyl acetate-hexane to give the title compound (227 mg, 57%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hr
  3. extractionextracted with ethyl acetate (50 ml×2)
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane
  8. customethyl acetate=2:1-1:1 and recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e09314ceb25f40e79507bb1327a6015c
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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