Phthalimide → (1R,3R)-N-[3-(3-pyridyl)cyclopentyl]phthalimide

HRID 655165Notes

Reaction equation

HRID 655165 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]2[CH2:11][CH2:10][C@H:9](O)[CH2:8]2)[CH:2]=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.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CCOC(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]2[CH2:11][CH2:10][C@@H:9]([N:17]3[C:16](=[O:18])[C:15]4=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]4[C:13]3=[O:23])[CH2:8]2)[CH:2]=1

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59486133(1S,3R)-3-(3-pyridyl)cyclopentanol

Product 1

HCID 68508356(1R,3R)-N-[3-(3-pyridyl)cyclopentyl]phthalimideYield 89%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (1S,3R)-3-(3-pyridyl)cyclopentanol (3.95 g, 24.2 mmol) in THF (80 mL) was cooled to 4° C. and treated with phthalimide (3.91 g, 26.6 mmol), Diisopropylazodicarboxylate (5.24 mL, 26.6 mmol) and triphenylphosphine (6.98 g, 26.6 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with EtOAc, and washed with H2O and brine. The organic layers was dried over Na2SO4. After concentration under reduced pressure, the residue was purified by column chromatography (Hexane/EtOAc=4/1) to yield (1R,3R)-N-[3-(3-pyridyl)cyclopentyl]phthalimide (6.27 g, 89%) as colorless powder.

Workup

  1. washwashed with H2O and brine
  2. dry with materialThe organic layers was dried over Na2SO4
  3. concentrationAfter concentration under reduced pressure
  4. customthe residue was purified by column chromatography (Hexane/EtOAc=4/1)

Sources & evidence

ORD record
ord-fee799cd765e4c69a025c936e6d3371a
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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