tert-butyl [7-(hepta-1,6-dien-4-yl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate → tert-butyl [7-(cyclopent-3-en-1-yl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate
Reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:16]=[CH:15][C:14]([CH:17]([CH2:21][CH:22]=C)[CH2:18][CH:19]=C)=[C:13]2[C:9]=1[C:10](=[O:25])[N:11]([CH3:24])[CH2:12]2)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:21][CH:22]=[CH:19][CH2:18]2)=[C:13]2[C:9]=1[C:10](=[O:25])[N:11]([CH3:24])[CH2:12]2)([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
To a solution of tert-butyl[7-(hepta-1,6-dien-4-yl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate (Compound 243D, 180 mg, 0.50 mmol) in DCM (10 mL) was added (benzylidene)bis(tricyclohexylphosphine)ruthenium(IV)dichloride (21 mg, 0.025 mmol). The resulting mixture was stirred at rt under nitrogen. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (ISCO Combi-flash system, eluting with 10-30% EtOAc/Heptane) to give the title compound as a white solid, 150 mg, 90% yield. 1H NMR (CDCl3): 1.54 (s, 9H), 2.43-2.48 (m, 2H), 2.81-2.86 (m, 2H), 3.18 (s, 3H), 3.45 (m, 1H), 4.32 (s, 2H), 5.80-5.84 (m, 2H), 7.35 (d, J=8.6 Hz, 1H), 8.12 (d, J=8.6 Hz, 1H), 9.53 (br s, 1H). MS (ES+): m/z=329.13 [MH+]. HPLC: tR=4.65 min (ZQ3, polar—5 min).
Workup
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel chromatography (ISCO Combi-flash system, eluting with 10-30% EtOAc/Heptane)
Sources & evidence
- ORD record
- ord-897920092f7e4409a1222a64d1e1998a
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399433B2
Reaction notes
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