Dimethyl Sulfoxide → 2-[(7S)-1-benzyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]-1H-isoindole-1,3(2H)-dione

HRID 1392089Notes

Reaction equation

[CH2:1]([N:8]([C@H:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)C=C)[C:9](=[O:25])[CH:10]([N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24])[CH2:11][CH:12]=[CH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=O>C1(C)C=CC=CC=1.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[CH2:26]([N:8]1[C@H:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:13]=[CH:12][CH2:11][CH:10]([N:14]2[C:15](=[O:24])[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]2=[O:23])[C:9]1=[O:25])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N-benzyl-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-[(1S)-1-phenylprop-2-en-1-yl]pent-4-enamide (5b) (230 mg) dissolved in Toluene (25 mL) at 80° C. under N2 was added Grubbs catalyst (2nd generation) (22 mg) and the reaction mixture was stirred at 80° C. for 2 h, then cooled to RT. DMSO (0.1 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%, 15% EtOAc/hexanes) to give a diastereomeric mixture (1.5:1) of the title compound. (168 mg, 78%).

Workup

temperaturecooled to RT
stirringthe mixture stirred for 1 h
concentrationconcentrated
customThe crude product was directly purified via flash chromatography (gradient—5%, 10%, 15% EtOAc/hexanes)

Sources & evidence

ORD record: ord-648a9037148a43ce8d0507b6869805e7
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342007B2

Reaction notes

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