HCID 22851568, compound → HCID 22851571, compound

HRID 1033293Notes

Reaction equation

HRID 1033293 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-558c4726fc0f4e8cb036a7702204f568
Source dataset
uspto-grants-1994_05
Patent number
US05310743

Reaction notes

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