1-Allyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexanecarboxylic acid ethyl ester → 4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-((E)-propenyl)-cyclohexanecarboxylic acid ethyl ester

HRID 1944735Notes

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

1-Allyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexanecarboxylic acid ethyl ester (Intermediate 73, 975 mg, 2.86 mmol) was dissolved in ethanol (13.900 mL) in a roundbottom flask with reflux condensor. The flask was charged with rhodium(III) chloride (32.5 mg, 0.143 mmol), and the reaction mixture was heated to 75° C. and stirred for 18 hr, then filtered and concentrated in vacuo to yield the title compound as a brown oil (965 mg, 99%) which was taken to the next step without further purification.

Workup

temperaturewith reflux condensor
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-39db7fb3b74546b2981abc9a3568eb83
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394858B2

Reaction notes

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