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

HRID 1610179노트

반응식

HRID 1610179 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 10313134Manganese(2+) dichloride촉매HCID 887Methanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-e09314ceb25f40e79507bb1327a6015c
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

반응 노트

불러오는 중…