HCID 68759633, compound → HCID 49834555, compound

HRID 1627067Notes

Reaction equation

HRID 1627067 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14]2)=[CH:9][C:8]=1[C:19]([F:22])([F:21])[F:20])[CH3:2]>CCOC(C)=O.[Pd]>[O:18]=[C:15]1[CH2:16][CH2:17][C@@H:13]([C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:23])=[C:8]([C:19]([F:20])([F:21])[F:22])[CH:9]=2)[CH2:14]1

Participants

4

Reactant 1

HCID 68759633HCID 68759633, compound

Product 1

HCID 49834555HCID 49834555, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-3-[4-(3-oxo-cyclopentyl)-2-trifluoromethyl-phenyl]-acrylic acid ethyl ester (preparation 7, 1.55 g) in EtOAc (40 mL) containing Pd/C (300 mg) was hydrogenated overnight at rt. The catalyst was removed by filtration through Celite, and the filtrate was concentrated under reduced pressure, affording the title compound as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.54-7.48 (m, 1H), 7.39-7.24 (m, 2H), 4.14 (q, 2H), 3.51-3.35 (m, 1H), 3.12 (t, 2H), 2.75-2.23 (m, 7H), 2.05-1.90 (m, 1H), 1.25 (t, 3H).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-35e0a3f9f8db4d37885f9acbe25a18eb
Source dataset
uspto-grants-2014_07
Patent number
US08785494B2

Reaction notes

Loading…