N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)-N-(dicyclopropylmethyl)acrylamide → (5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(dicyclopropylmethyl)-5,6-dihydropyridin-2(1H)-one

HRID 1048346Notes

Reaction equation

HRID 1048346 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH:29]=[CH2:30])[C@H:9]([N:17]([CH:22]([CH:26]2[CH2:28][CH2:27]2)[CH:23]2[CH2:25][CH2:24]2)[C:18](=[O:21])C=C)[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[N:17]([CH:22]([CH:26]3[CH2:27][CH2:28]3)[CH:23]3[CH2:24][CH2:25]3)[C:18](=[O:21])[CH:30]=[CH:29]2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 67999897N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)-N-(dicyclopropylmethyl)acrylamide

Product 1

HCID 67998565(5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(dicyclopropylmethyl)-5,6-dihydropyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2.1 g (4.77 mmol) of N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)-N-(dicyclopropylmethyl)acrylamide (Example 115, Step G) in 50 mL of DCE was added 160 mg of 1,3-bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)(dichlorophenylmethylene)(tricyclohexylphosphine)ruthenium (“Grubb's 2nd Generation Catalyst”). The resulting mixture was degassed two times and then heated to 70° C. for 18 h. Another 160 mg of Grubb's 2nd Generation Catalyst was added at that time and heating was continued for another 18 h. The reaction mixture was cooled to room temperature. The solvent was removed and the residue was purified by chromatography on silica gel (eluent: hexane/ethyl acetate, 90/10 to 20/80) to give the title compound.

Workup

  1. customThe resulting mixture was degassed two times
  2. additionAnother 160 mg of Grubb's 2nd Generation Catalyst was added at that time
  3. temperatureheating
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customThe solvent was removed
  6. customthe residue was purified by chromatography on silica gel (eluent: hexane/ethyl acetate, 90/10 to 20/80)

Sources & evidence

ORD record
ord-bafaa60ad06140a09b0ef628765f5855
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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