Hydrogen Peroxide → HCID 86670969、化合物

HRID 515339ノート

反応式

HRID 515339 の反応式
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([CH:6]=[C:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[F:32].B#B.[O:35]1CCCC1.[OH-].[Na+].OO.[Cl-].[NH4+]>O.C(O)C>[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([CH:6]([OH:35])[CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]([OH:29])([C:21]([F:22])([F:23])[F:24])[C:25]([F:28])([F:26])[F:27])=[CH:18][CH:19]=3)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[F:32]

参加物

9

反応物 6

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 6328200DiboronHCID 866709702-(4-((4-(4-Amino-3-fluorobenzylidene)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

生成物 1

HCID 86670969HCID 86670969、化合物収率 9%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

2-(4-((4-(4-Amino-3-fluorobenzylidene)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (1.384 mmol, 0.64 g) was cooled to 0° C. and 1M diborane solution in tetrahydrofuran (5.54 mmol, 5.54 mL) added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The mixture was cooled to 0° C. and ethanol slowly added. Sodium hydroxide (8.30 mmol, 0.332 g) in water (20 mL) was then added slowly with stirring, followed by hydrogen peroxide (24.91 mmol, 2.421 g). The mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into an aqueous solution of ammonium chloride (50 mL) and the mixture extracted with dichloromethane (3×100 mL). The combined organic phase was then washed with water (50 mL) and brine (50 mL) and the organic phase dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting with 2% to 10% methanol/dichloromethane) to afford the title compound (60 mg).

後処理

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringwith stirring
  3. stirringThe mixture was stirred at room temperature for 16 hours
  4. extractionthe mixture extracted with dichloromethane (3×100 mL)
  5. washThe combined organic phase was then washed with water (50 mL) and brine (50 mL)
  6. dry with materialthe organic phase dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (eluting with 2% to 10% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-1e78408ab24a40c7acbd152a08f3610c
出典データセット
uspto-grants-2015_08
特許番号
US09108939B2

反応ノート

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