Acetic Acid → HCID 89814194, compound

HRID 522703Notes

Reaction equation

HRID 522703 reaction equation
C([N:8](CC1C=CC=CC=1)[CH2:9][CH2:10][C:11]([F:14])([CH3:13])[CH3:12])C1C=CC=CC=1.[C:22]([OH:25])(=[O:24])[CH3:23]>CO.[Pd]>[C:22]([OH:25])(=[O:24])[CH3:23].[F:14][C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][NH2:8]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 89814611HCID 89814611, compound

Product 1

HCID 89814194HCID 89814194, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

Treat a solution of N,N-dibenzyl-3-fluoro-3-methylbutan-1-amine (18.03 g, 63.2 mmol) in MeOH (150 mL) and acetic acid (7.23 mL, 126 mmol) with 10% Pd/C (3.36 g, 3.16 mmol) and hydrogenate (345 kPa) for 2.5 days. Add additional palladium on carbon (1 g) and hydrogenate the mixture (345 kPa) overnight. Filter the mixture through diatomaceous earth, rinse well with MeOH and concentrate the filtrate to dryness to afford the title compound MS (m/z): 106.1 (M-AcOH+1).

Workup

  1. filtrationFilter the mixture through diatomaceous earth
  2. washrinse well with MeOH
  3. concentrationconcentrate the filtrate to dryness

Sources & evidence

ORD record
ord-f7cfff13637848e39c1607cdfe1ad2b3
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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