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Allyltrimethylsilane → tert-butyl [7-(hepta-1,6-dien-4-yl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate

HRID 1948060
Notes
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Reaction equation

HRID 1948060 reaction equation
C(O[CH:5]([C:9]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:14]2[C:10]=1[CH2:11][N:12]([CH3:27])[C:13]2=[O:26])[CH2:6][CH:7]=[CH2:8])(=O)C.[Br-].[Br-].[Br-].[In+3].[CH2:32]([Si](C)(C)C)[CH:33]=[CH2:34]>C(Cl)Cl>[C:22]([O:21][C:19](=[O:20])[NH:18][C:15]1[CH:16]=[CH:17][C:9]([CH:5]([CH2:34][CH:33]=[CH2:32])[CH2:6][CH:7]=[CH2:8])=[C:10]2[C:14]=1[C:13](=[O:26])[N:12]([CH3:27])[CH2:11]2)([CH3:25])([CH3:24])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 69808AllyltrimethylsilaneHCID 167051indium(III)bromideHCID 672543181-{7-[(tert-butoxycarbonyl)amino]-2-methyl-1-oxo-2,3-dihydro-1H-isoindol-4-yl}but-3-en-1-yl acetate2×

Product 1

HCID 58293015tert-butyl [7-(hepta-1,6-dien-4-yl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a solution of 1-{7-[(tert-butoxycarbonyl)amino]-2-methyl-1-oxo-2,3-dihydro-1H-isoindol-4-yl}but-3-en-1-yl acetate (Compound 243E, 895 mg, 2.39 mmol) in DCM (30 mL) were added indium tribromide (85 mg, 0.24 mmol), followed by the addition of allyltrimethylsilane (550 mg, 4.8 mmol) in DCM (0.5 mL). The resulting mixture was refluxed under nitrogen overnight. The solvent was evaporated and the residue was purified by silica gel chromatography (ISCO Combi-flash system, eluting with 10-50% EtOAc/Heptane) to give the desired product as a white solid, 180 mg. The unreacted starting material was recovered and resubjected to the reaction using 2.0 eq. allyltrimethylsilane and 0.2 eq. InBr3. The mixture was refluxed overnight. The solvent was evaporated and the residue was purified by silica gel chromatography (ISCO Combi-flash system, eluting with 10-50% EtOAc/Heptane) to give the desired product as a white solid, 125 mg. Totally 305 mg, 36% yield. 1H NMR (CDCl3): 1.53 (s, 9H), 2.34-2.47 (m, 4H), 2.67 (m, 1H), 3.16 (s, 3H), 4.27 (s, 2H), 4.92-4.99 (m, 4H), 5.55-5.64 (m, 2H), 7.29 (d, J=8.6 Hz, 1H), 8.16 (d, J=8.6 Hz, 1H), 9.52 (br s, 1H). MS (ES+): m/z=379.13 [MNa+]. HPLC: tR=4.83 min (ZQ3, polar—5 min).

Workup

  1. temperatureThe resulting mixture was refluxed under nitrogen overnight
  2. customThe solvent was evaporated
  3. customthe residue was purified by silica gel chromatography (ISCO Combi-flash system, eluting with 10-50% EtOAc/Heptane)

Sources & evidence

ORD record
ord-1741cc5beb4e43438f0a986a53138ddf
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399433B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes