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

HRID 655170Notes

Reaction equation

HRID 655170 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 67133573cis-3-(3-Pyridyl)cyclohexanol

Product 1

HCID 67133459trans-N-[3-(3-pyridyl)cyclohexyl]phthalimideYield 60%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of cis-3-(3-pyridyl)cyclohexanol (5.00 g, 28.2 mmol) in THF (100 mL) was cooled to 4° C. and treated with phthalimide (4.56 g, 31.0 mmol), Diisopropylazodicarboxylate (6.10 mL, 31.0 mmol) and triphenylphosphine (8.13 g, 31.0 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 trans-N-[3-(3-pyridyl)cyclohexyl]phthalimide (5.18 g, 60%) 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-bd7ebe3048d34962abed581481ad855f
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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