HCID 67109597, compound → HCID 67109671, compound

HRID 455298Notes

Reaction equation

HRID 455298 reaction equation
C([O:8][C:9]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:10]=1[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])C1C=CC=CC=1.[H][H]>CCO.C(OCC)(=O)C.[Pd]>[F:24][C:22]1[CH:21]=[CH:20][C:10]([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[C:9]([OH:8])[CH:23]=1

Participants

6

Reactant 2

HCID 67109597HCID 67109597, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67109671HCID 67109671, compoundYield 101.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 2-(benzyloxy)-4-fluorobenzylcarbamate (Example 14; 9 mmol) in EtOH (80 ml) and ethyl acetate (240 ml) was treated with 1 atm of hydrogen at 25° C. over 10% Pd/C (0.4 gr) for 24 hours. The catalyst was removed by filtration through celite, washed with EtOH and the filtrate was concentrated to afford the title compound (2.2 g) as a yellow solid.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. washwashed with EtOH
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-56b64e6ec5e74b188e5eddf5ffc60d44
Source dataset
uspto-grants-2013_07
Patent number
US08497270B2

Reaction notes

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