Phthalimide → HCID 86594646, compound

HRID 1243171Notes

Reaction equation

HRID 1243171 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.[C:34]1(=[O:44])[NH:38][C:37](=[O:39])[C:36]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:35]12.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][C@@H:7]1[CH2:11][CH2:10][C@H:9]([N:38]2[C:34](=[O:44])[C:35]3[C:36](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:37]2=[O:39])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58715064Cyclopentanol, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, trans-

Product 1

HCID 86594646HCID 86594646, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (±)-trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol (1.1 g, 5.08 mmol) (from Example 10a supra), triphenylphosphine (3.2 g, 12.20 mmol) (Aldrich) and phthalimide (1.8 g, 12.20 mmol) (Aldrich) in anhydrous tetrahydrofuran (45 mL) was cooled to 0° C. To this was added dropwise diethyl azodicarboxylate (2.1 mL, 2.3 g, 12.20 mmol) (Aldrich) and the resulting solution was allowed to slowly warm to room temperature. After stirring overnight the reaction mixture was partitioned between ethyl acetate and water. The organic layer was collected, dried over sodium sulfate, filtered and concentrated and the residue was purified by chromatography on a silica gel column using a 0–35% ethyl acetate in hexanes gradient to give (±)-cis-2-[3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-isoindole-1,3-dione as a white solid. (Yield 1.52 g, 87%).

Workup

  1. customwas partitioned between ethyl acetate and water
  2. customThe organic layer was collected
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-7bcd77a023a9484198b287c4b3807fc4
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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