HCID 67401817, compound → HCID 67402546, compound

HRID 1186419Notes

Reaction equation

HRID 1186419 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]([O:22][Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])[C:18]([F:21])([F:20])[F:19])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[F:20][C:18]([F:19])([F:21])[CH:17]([CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)[O:22][Si:23]([CH2:24][CH3:25])([CH2:28][CH3:29])[CH2:26][CH3:27]

Participants

4

Reactant 1

HCID 67401817HCID 67401817, compound

Product 1

HCID 67402546HCID 67402546, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

Ten percent palladium/carbon (170 mg) was suspended in ethanol (5.0 mL). To this, an ethanol solution (25 mL) of 1-benzyloxycarbonyl-4-[2,2,2-trifluoro-1-(triethylsiloxy)-ethyl]piperidine (1.69 g, 3.92 mmol) was added and the mixture was stirred under a hydrogen atmosphere at room temperature for 2.5 hours. The reaction mixture was filtered through Celite and the solvent was evaporated off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform) to give 4-[2,2,2-trifluoro-1-(triethylsiloxy)ethyl]piperidine (1.15 g, yield: 99%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was evaporated off under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-caea788756ab4cdfb567fe3950e7f54d
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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