(E)-3-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-acrylic Acid Methyl Ester → 3-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-propionic Acid Methyl Ester

HRID 220890Notes

Reaction equation

HRID 220890 reaction equation
[CH3:1][O:2][C:3](=[O:25])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([C:12]([N:14]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]3[CH:21]=[CH:22][CH:23]=[CH:24][C:15]2=3)=[O:13])=[CH:8][CH:7]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([N:14]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]3[CH:21]=[CH:22][CH:23]=[CH:24][C:15]2=3)=[O:13])=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 57555201(E)-3-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-acrylic Acid Methyl Ester

Product 1

HCID 575553603-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-propionic Acid Methyl EsterYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(E)-3-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-acrylic acid methyl ester from Example E65.2 (485 mg, 1.44 mmol) was dissolved in methanol (60 ml) and hydrogenated over 10% Pd/C catalyst (214 mg) for 2 h. The mixture was filtered through Celite® filter agent and the filtrate was concentrated in vacuo to yield the title compound (415 mg, 85%).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. filtrationfilter agent
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b482ab7f9e9c439cb28a22b72a12f6a3
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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