HCID 53753364, compound → HCID 22632212, compound

HRID 2416706Notes

Reaction equation

HRID 2416706 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:14][C:15]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:16]=1[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[O:20])[CH2:9][C:10]([F:13])([F:12])[F:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]([CH2:14][C:15]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:16]=1[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:9][C:10]([F:11])([F:12])[F:13])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 53753364HCID 53753364, compound

Product 1

HCID 22632212HCID 22632212, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 10% Pd/C (5 g, 4.7 mmol, prewetted with DMF) was added a solution of methyl 2-[N-(tert-butoxycarbonyl)-N-(2,2,2-trifluoroethyl)amino]methyl-4-methoxycinnamate (45.85 g, 113 mmol) in methanol (100 mL). The mixture was shaken under hydrogen (50 psi) in a Parr apparatus for 6 hr, then was filtered through a pad of celite® to remove the catalyst. The filtrate was concentrated to afford the title compound (43.71 g, 95%) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 7.11 (d, J=8 Hz, 1H), 6.78 (dd, 1H), 6.65 (s, 1H), 4.63 and 4.60 (2s, 2H), 3.84 and 3.70 (2m, 2H), 3.77 (s, 3H), 3.66 (s, 3H), 2.86 (t, 2H), 2.53 (t, 2H), 1.50 and 1.44 (2s, 9H).

Workup

  1. filtrationwas filtered through a pad of celite®
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3cd3d3eae2554a3f99d6b99ddb5fc1dd
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

Loading…