HCID 69481033, compound → HCID 69480049, compound

HRID 856063Notes

Reaction equation

HRID 856063 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pt]=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 69481033HCID 69481033, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69480049HCID 69480049, compoundYield 40.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 4-[3-(4-chlorophenyl)-2-propenyloxy]piperidine-1-carboxylate (0.37 g, 1.05 mmol) prepared in Reference example 112 and platinum oxide (37 mg) in ethanol (10 ml), was stirred at room temperature under atmospheric pressure of hydrogen. The reaction mixture was filtered through Celite, and the filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to afford tert-butyl 4-[3-(4-chlorophenyl)propoxy]piperidine-1-carboxylate (0.151 g, yield 40%) as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under a reduced pressure
  3. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-fafe82953feb41c0a026202b96b9a1e8
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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