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

HRID 1610167ノート

反応式

HRID 1610167 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 10313134Manganese(2+) dichloride触媒HCID 887Methanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-4fb08f691008481c824238288da89a46
出典データセット
uspto-grants-2006_01
特許番号
US06982348B2

反応ノート

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