HCID 54071285, compound → HCID 22632255, compound

HRID 2416700Notes

Reaction equation

HRID 2416700 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:20][C:21]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:22]=1[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[O:26])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]([CH2:20][C:21]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:22]=1[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 54071285HCID 54071285, compound

Product 1

HCID 22632255HCID 22632255, compoundYield 98.5%

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-(4-trifluoromethylbenzyl)aminomethyl]-4-methoxycinnamate (34.52 g, 72 mmol) in methanol (100 mL). The mixture was shaken under hydrogen (50 psi) in a Parr apparatus for 7 hr, then was filtered through a pad of celite® to remove the catalyst. The filtrate was concentrated to afford the title compound (34.15 g, 98%) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 7.58 (d, J=8.1 Hz, 2H), 7.31 (br s, 2H), 7.09 (d, J=8.4 Hz, 1H), 6.76 (dd, 1H), 6.66 (s, 1H), 4.47 (br s, 2H), 4.40 (br s, 2H), 3.76 (s, 3H), 3.63 (s, 3H), 2.79 (br s, 2H), 2.47 (t, 2H), 1.48 (s, 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-97e1499761cd4898896b09c671438035
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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