HCID 22851568, compound → HCID 22851571, compound

HRID 1736963Notes

Reaction equation

HRID 1736963 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C([N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[CH2:17][C@H:16]1[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)C1C=CC=CC=1>[Pd].O1CCOCC1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:28]([C@@H:16]1[CH2:17][CH:18]([NH:21][C:22](=[O:27])[C:23]([F:26])([F:24])[F:25])[CH2:19][CH2:20][NH:15]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 1

HCID 22851568HCID 22851568, compound

Product 1

HCID 22851571HCID 22851571, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

3.0 g of 10% palladium catalyst on carbon are added to a solution of 19.3 g (39.4 mmol) of (2R,4RS)-N-(1,2-dibenzyl-4piperidyl)trifluoroacetamide trifluoroacetate in 160 ml of dioxane under nitrogen, and hydrogenation is carried out under atmospheric pressure at room temperature. The reaction mixture is freed of catalyst over Celite® and the residue is washed with dioxane. The filtrate is evaporated to dryness and dried under high vacuum, resulting in the title compound which is used further without further purification; TLC: methylene chloride/methanol/conc. ammonia (90:9:1) Rf =0.24 and 0.3 (two poorly separated diastereomers)

Workup

  1. customis carried out under atmospheric pressure at room temperature
  2. washthe residue is washed with dioxane
  3. customThe filtrate is evaporated to dryness
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-1dcc28426956419b97834e1fc3ce2e98
Source dataset
uspto-grants-1996_07
Patent number
US05541195

Reaction notes

Loading…