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

HRID 1610167Notes

Reaction equation

HRID 1610167 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:35])[CH:9]([NH:21][C:22]([C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([CH3:34])=[CH:26][CH:25]=2)=[O:23])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO.[Cl-].[Mn+2].[Cl-]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:35])[CH:9]([NH:21][C:22]([C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([CH3:34])=[CH:26][CH:25]=2)=[O:23])[CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22261573N-(2-(4-fluorophenyl)-2-oxo-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-4-methyl-1-naphthalenecarboxamide

Product 1

HCID 22261907N-(2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-4-methyl-1-naphthalenecarboxamideYield 82.3%

Reagents, catalysts & solvents 2

HCID 10313134Manganese(2+) dichlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(2-(4-fluorophenyl)-2-oxo-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-4-methyl-1-naphthalenecarboxamide (400 mg, 0.83 mmol) in methanol (30 ml) was added manganese (II) chloride (210 mg, 1.67 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction solution were added sodium borohydride (63 mg, 1.67 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), and the obtained crude crystal was washed with a mixed solvent of hexane:ethyl acetate=10:1 to give the title compound ((1RS,2SR) form: (1RS,2RS) form=1:2, 329 mg, 82%).

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:ethyl acetate=2:1)
  8. customthe obtained crude crystal
  9. washwas washed with a mixed solvent of hexane

Sources & evidence

ORD record
ord-4fb08f691008481c824238288da89a46
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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