Ethyl Acrylate → HCID 68759633, compound

HRID 1627066Notes

Reaction equation

HRID 1627066 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]2)=[CH:4][C:3]=1[C:14]([F:17])([F:16])[F:15].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CC([O-])=O.[Na+].[C:45]([O:49][CH2:50][CH3:51])(=[O:48])[CH:46]=[CH2:47]>CN(C=O)C.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:50]([O:49][C:45](=[O:48])[CH:46]=[CH:47][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]2)=[CH:4][C:3]=1[C:14]([F:17])([F:16])[F:15])[CH3:51]

Participants

8

Reactant 4

HCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 517045Sodium AcetateHCID 49834553(3R)-3-[4-Bromo-3-(trifluoromethyl)phenyl]cyclopentanone

Product 1

HCID 68759633HCID 68759633, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To a mixture of (R)-3-(4-bromo-3-trifluoromethyl-phenyl)-cyclopentanone (Preparation 6, 1.96 g), tri(o-tolyl)phosphine (120 mg), Pd(OAc)2 (43 mg) and NaOAc (0.79 g) in DMF (13 mL) was added ethyl acrylate (0.79 g), and the reaction mixture was heated to 130° C. for 3 h. The mixture was diluted with EtOAc and washed with water. The organic phase was dried and concentrated in vacuo, and the residue was purified by flash chromatography using a gradient of heptane and EtOAc to obtain the title compound. 1H NMR (300 MHz, CDCl3) δ 8.09-7.97 (m, 1H), 7.70 (d, 1H), 7.58 (d, 1H), 7.53-7.38 (m, 1H), 6.40 (d, 1H), 4.28 (q, 2H), 3.58-3.40 (m, 1H), 2.72 (dd, 1H), 2.58-2.26 (m, 4H), 2.10-1.92 (m, 1H), 1.34 (t, 3H).

Workup

  1. washwashed with water
  2. customThe organic phase was dried
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c271d8cbf2494c0da258af7e751838fd
Source dataset
uspto-grants-2014_07
Patent number
US08785494B2

Reaction notes

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