HCID 18621154, compound → HCID 18621150, compound

HRID 1861658Notes

Reaction equation

HRID 1861658 reaction equation
C(OC([NH:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:16][CH2:15]1)=O)C1C=CC=CC=1>O1CCCC1.O.[Pd]>[C:24]([Si:21]([CH3:23])([CH3:22])[O:20][CH:17]1[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][NH2:11])[CH2:15][CH2:16]1)([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 1

HCID 18621154HCID 18621154, compound

Product 1

HCID 18621150HCID 18621150, compoundYield 28.9%

Reagents, catalysts & solvents 2

HCID 23219155Palladium hydrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(benzyloxycarbonyl)-2-[4-(t-butyldimethyl siloxy)-1-piperidyl] ethylamine (1.47 g) in tetrahydrofuran (37 ml), there was added 20% palladium hydroxide-on-carbon (100 mg). The resulting mixture was stirred over 2 days under a hydrogen gas atmosphere. The mixture was filtered through celite to remove the palladium hydroxide-on-carbon and the resulting filtrate was concentrated under reduced pressure. The resulting oily product was purified through the silica gel column chromatography to thus give the title compound (Reference Compound 5-1, 0.28 g).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customto remove the palladium hydroxide-on-carbon
  3. concentrationthe resulting filtrate was concentrated under reduced pressure
  4. customThe resulting oily product was purified through the silica gel column chromatography

Sources & evidence

ORD record
ord-8ba5aec8bc9145fca521a811b4583164
Source dataset
uspto-grants-2003_03
Patent number
US06534499B2

Reaction notes

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