Water → HCID 23081330, compound

HRID 856068Notes

Reaction equation

HRID 856068 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].[F:17][C:18]([F:28])([F:27])[C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.O>C1COCC1>[F:17][C:18]([F:27])([F:28])[C:19]1[CH:26]=[CH:25][C:22]([CH2:23][O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 23081330HCID 23081330, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl 4-hydroxypiperidine-1-carboxylate (1.88 g, 9.34 mmol) was dissolved in THF (20 ml). Sodium hydride (411 mg, 10.3 mmol) was added to this solution while cooling in an ice-bath, and the mixture was stirred for 1 hour. 4-(Trifluoromethyl) benzylbromide (2.23 g, 9.34 mmol) was added to the mixture, which was stirred at room temperature for 2 hours. Water was added to the reaction mixture, which was extracted with methylene chloride. The extract was dried over magnesium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) to afford tert-butyl 4-(4-trifluoromethylbenzyloxy)piperidine-1-carboxylate (2.56 g, yield 76%) as a pale yellow oil.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. stirringwas stirred at room temperature for 2 hours
  3. extractionwas extracted with methylene chloride
  4. dry with materialThe extract was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)

Sources & evidence

ORD record
ord-03720f9e6a0e42fcb59bff6956f4d1e1
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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