Phthalimide → HCID 23130721, compound

HRID 2080164Notes

Reaction equation

HRID 2080164 reaction equation
[O:1]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15]O)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[O:1]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:21]2[C:17](=[O:27])[C:18]3[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:20]2=[O:22])=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23130408HCID 23130408, compound

Product 1

HCID 23130721HCID 23130721, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-phenoxymethyl-pyridin-2-yl)-methanol described in Preparation Example 187 (167 mg, 0.776 mmol) in tetrahydrofuran (4 mL) were added phthalimide (126 mg, 0.856 mmol), triphenylphosphine (244 mg, 0.930 mmol) and diethyl azodicarboxylate (424 μL, 0.931 mmol, 40% toluene solution) at 0° C., and the solution was stirred at room temperature for 30 minutes. The reaction solution was partitioned with water and ethyl acetate. The organic layer was separated, washed with brine, and then, dried over anhydrous magnesium sulfate. The organic layer was filtered, then, the solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (heptane/ethyl acetate=1/1), and the title compound (383 mg, quantitatively) was obtained as a white solid.

Workup

  1. customThe reaction solution was partitioned with water and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe organic layer was filtered
  6. customthe solvent was evaporated in vacuo
  7. customthe residue was purified by silica gel column chromatography (heptane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-69b12b41da53424386b234098da30140
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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