Phthalimide → cis-N-[3-(3-pyridyl)cyclohexyl]phthalimide

HRID 655174Notes

Reaction equation

HRID 655174 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@H:7]2[CH2:12][CH2:11][CH2:10][C@H:9](O)[CH2:8]2)[CH:2]=1.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]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[CH2:12][CH2:11][CH2:10][C@H:9]([N:18]3[C:17](=[O:19])[C:16]4=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]4[C:14]3=[O:24])[CH2:8]2)[CH:2]=1

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 67133888trans-3-(3-Pyridyl)cyclohexanol

Product 1

HCID 67133879cis-N-[3-(3-pyridyl)cyclohexyl]phthalimideYield 24.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of trans-3-(3-pyridyl)cyclohexanol (3.99 g, 22.5 mmol) in THF (90 mL) was cooled to 4° C. and treated with phthalimide (3.65 g, 24.8 mmol), Diisopropylazodicarboxylate (4.88 mL, 24.8 mmol) and triphenylphosphine (6.50 g, 24.8 mmol). The reaction mixture was stirred at room temperature for 30 min. 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 cis-N-[3-(3-pyridyl)cyclohexyl]phthalimide (1.66 g, 24%) 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-4b9606cdfae640f7bb7129839eb53282
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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