Phthalimide → HCID 70204323, compound

HRID 1378387Notes

Reaction equation

HRID 1378387 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([C:16]([F:19])([F:18])[F:17])[C@H:13]([CH2:20]O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1(=[O:32])[NH:26][C:25](=[O:27])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([C:16]([F:17])([F:18])[F:19])[C@H:13]([CH2:20][N:26]2[C:25](=[O:27])[C:24]3=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]3[C:22]2=[O:32])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 70204259HCID 70204259, compound

Product 1

HCID 70204323HCID 70204323, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 250 ml of absolute tetrahydrofuran, is dissolved 8.0 g (26.4 mmol) of trans-1-benzyloxycarbonyl-3-hydroxymethyl-4-trifluoromethylpyrrolidine. To the above solution, are added 4.27 g (29.0 mmol) of phthalimide and 8.30 g (31.7 mmol) of triphenylphosphine. Further, 5.0 ml (31.7 mmol) of azo dicarboxylic acid diethyl ester is added dropwise to the above solution on cooling with ice. After stirring at room temperature for 3 hours, the reaction mixture was concentrated under reduced pressure, and diethyl ether was added to the concentrated mixture to give a precipitate. The resulting precipitate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (elusion solvent; chloroform/n-hexane (4/1→8/1)) to give 9.72 g of the objective substance as a colorless powder (yield 85.2%).

Workup

  1. temperatureon cooling with ice
  2. concentrationthe reaction mixture was concentrated under reduced pressure, and diethyl ether
  3. additionwas added to the concentrated mixture
  4. customto give a precipitate
  5. customThe resulting precipitate was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified with silica gel column chromatography (elusion solvent; chloroform/n-hexane (4/1→8/1))

Sources & evidence

ORD record
ord-4da255477fc04024aec64f62cfed224b
Source dataset
uspto-grants-1997_09
Patent number
US05668147

Reaction notes

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