Dimethyl Sulfoxide → HCID 58691182, compound

HRID 1392093Notes

Reaction equation

HRID 1392093 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([CH2:29][CH:30]=C)[C:13]([N:15]([CH2:25][CH2:26][O:27][CH3:28])[C@H:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:17]=C)=[O:14].CS(C)=O>C1(C)C=CC=CC=1.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[CH3:28][O:27][CH2:26][CH2:25][N:15]1[C@H:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:17]=[CH:30][CH2:29][CH:12]([N:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]2=[O:1])[C:13]1=[O:14]

Participants

5

Reactant 2

HCID 679Dimethyl SulfoxideHCID 58691192HCID 58691192, compound

Product 1

HCID 58691182HCID 58691182, compound

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-(2-methoxyethyl)-N-[(1S)-1-phenylprop-2-en-1-yl]pent-4-enamide (6b) (524 mg) dissolved in Toluene (50 mL) at 80° C. under N2 was added Grubbs catalyst (2nd generation) (53 mg) and the reaction mixture was stirred at 80° C. for 1 h, then cooled to RT. DMSO (0.2 mL) was added to the reaction and the mixture stirred for 1 h, then concentrated. The crude product was directly purified via flash chromatography (gradient—5%, 10%, 20%, 30% EtOAc/hexanes) to give a diastereomeric mixture (1:1) of the title compound. (426 mg, 87%).

Workup

  1. temperaturecooled to RT
  2. stirringthe mixture stirred for 1 h
  3. concentrationconcentrated
  4. customThe crude product was directly purified via flash chromatography (gradient—5%, 10%, 20%, 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-28463be74c264daf8656020756e518b1
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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