Triphenylphosphine → cis 2-[3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-5,6-dichloro-isoindole-1,3-dione

HRID 905975Notes

Reaction equation

HRID 905975 reaction equation
[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][C@H:7]1[CH2:11][CH2:10][C@H:9](O)[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:48][C:49]1[CH:50]=[C:51]2[C:56](=[O:57])[NH:55][C:53](=[O:54])[C:52]2=[CH:58][C:59]=1[Cl:60]>CC1CCCO1>[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][C@@H:7]1[CH2:11][CH2:10][C@H:9]([N:55]2[C:56](=[O:57])[C:51]3[C:52](=[CH:58][C:59]([Cl:60])=[C:49]([Cl:48])[CH:50]=3)[C:53]2=[O:54])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2515434,5-DichlorophthalimideHCID 58715064Cyclopentanol, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, trans-

Product 1

HCID 86642299cis 2-[3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-5,6-dichloro-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent

Procedure

To a round bottomed flask was added trans 3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol (1.0 g, 4.62 mmol, prepared from WO2008065021), triphenylphosphine (1.52 g, 5.76 mmol) and 2-methyltetrahydrofuran (120 mL). Diisopropyl azodicarboxylate (1.23 mL, 6.25 mmol) was added over two minutes via syringe followed by 4,5-dichlorophthalimide (1.35 g, 6.25 mmol). The reaction was stirred overnight and evaporated. The reaction was repeated and the combined material was purified by column chromatography (160 g SiO2, EtOAc in hexane) to give cis 2-[3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-5,6-dichloro-isoindole-1,3-dione, a yellowish solid (2.0 gm, 52% yield)

Workup

  1. customevaporated
  2. customthe combined material was purified by column chromatography (160 g SiO2, EtOAc in hexane)

Sources & evidence

ORD record
ord-58f9c3e7181241a1a66dcc60ef94072b
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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