HCID 54069682, compound → HCID 18695942, compound

HRID 1870226Notes

Reaction equation

HRID 1870226 reaction equation
[CH3:1][O:2][CH:3]1[C:8](=[CH:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6][N:5]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:4]1>C1COCC1.[Pt]>[CH3:1][O:2][CH:3]1[CH:8]([CH2:9][O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:7][CH2:6][N:5]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:4]1

Participants

4

Reactant 1

HCID 54069682HCID 54069682, compound

Product 1

HCID 18695942HCID 18695942, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of intermediate (3a) (0.043 mol) in THF (250 ml) was hydrogenated with platinum on activated carbon (5%) (3 g) as a catalyst. After uptake of H2 (1equiv.), the catalyst was filtered off and the filtrate was evaporated. The residue was purified by high-performance liquid chromatography over LiChroprep RP-18® (750 g; 8 cm; DAC column; eluent A: (0.5% NH4OAc in H2O)/CH3OH 75/25; eluent B: CH3CN; step gradient). The pure fractions were collected and the solvent was evaporated, yielding 8.34 g (59.6%) of (±)-3-methoxy-4-[(phenylmethoxy)methyl]-1-(phenylmethyl)-piperidine (interm. 3b).

Workup

  1. filtrationAfter uptake of H2 (1equiv.), the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by high-performance liquid chromatography over LiChroprep RP-18® (750 g; 8 cm; DAC column; eluent A: (0.5% NH4OAc in H2O)/CH3OH 75/25; eluent B: CH3CN; step gradient)
  4. customThe pure fractions were collected
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c62617c2575f47be8ce8649ea69cbb2f
Source dataset
uspto-grants-2000_08
Patent number
US06096761

Reaction notes

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