HCID 86717927, compound → 1609346-06-6

HRID 2275852Notes

Reaction equation

HRID 2275852 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([NH:14]C(C1C=CC=CC=1)CO)([CH3:13])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]>C(O)C.[OH-].[Pd+2].[OH-]>[NH2:14][C:3]([CH3:13])([C:2]([F:1])([F:24])[F:25])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:9])[CH3:10]

Participants

4

Reactant 1

HCID 86717927HCID 86717927, compound

Product 1

HCID 901360511609346-06-6

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Under argon, 39 g (107.6 mmol) of tert-butyl {3,3,3-trifluoro-2-[(2-hydroxy-1-phenylethyl)amino]-2-methyl-propyl}carbamate Example 244A were initially charged in ethanol (700 ml), and 5.44 g (53.8 mmol) of palladium(II) hydroxide (20% on activated carbon, moistened with water about 60%) were added. The reaction mixture was hydrogenated at atmospheric pressure for 16 h. The mixture was then filtered through silica gel and concentrated. The residue was purified by silica gel chromatography (cyclohexane/ethyl acetate gradient: from 9/1 to 6/4). This gave 15.8 g (61% of theory) of the target compound.

Workup

  1. filtrationThe mixture was then filtered through silica gel
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (cyclohexane/ethyl acetate gradient: from 9/1 to 6/4)

Sources & evidence

ORD record
ord-8272f8652a6b470885ea8c9e04a8e0be
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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