Hydrogen Peroxide → HCID 86670969, compound

HRID 515339Notes

Reaction equation

HRID 515339 reaction equation
[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]

Participants

9

Reactant 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

Product 1

HCID 86670969HCID 86670969, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-1e78408ab24a40c7acbd152a08f3610c
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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