Phthalimide → trans-N-[3-(2-pyridyl)cyclopentyl]phthalimide

HRID 655139Notes

Reaction equation

HRID 655139 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@@H:7]1[CH2:11][CH2:10][C@H:9](O)[CH2:8]1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]1[CH2:11][CH2:10][C@H:9]([N:17]2[C:16](=[O:18])[C:15]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]3[C:13]2=[O:23])[CH2:8]1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 67133931cis-3-(2-Pyridyl)cyclopentanol

Product 1

HCID 59486139trans-N-[3-(2-pyridyl)cyclopentyl]phthalimideYield 45.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of cis-3-(2-pyridyl)cyclopentanol (1.86 g, 11.4 mmol) in THF (100 mL) was cooled to 0° C. and treated with phthalimide (1.85 g, 12.5 mmol), diethylazodicarboxylate (2.2 M in toluene, 5.7 mL, 11.4 mmol) and triphenylphosphine (3.29 g, 12.5 mmol). The reaction mixture was stirred at room temperature for overnight. The solvent was removed, and the crude product was purified by column chromatography (Hexane/EtOAc=3/1→2/1→1/1) to yield trans-N-[3-(2-pyridyl)cyclopentyl]phthalimide (1.52 g, 41%) as a colorless powder.

Workup

  1. customThe solvent was removed
  2. customthe crude product was purified by column chromatography (Hexane/EtOAc=3/1→2/1→1/1)

Sources & evidence

ORD record
ord-d8c7abab03484874a8b8afc7b0f0e6ab
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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