Cyclopentanol → HCID 22385744, compound

HRID 857865Notes

Reaction equation

HRID 857865 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([NH:9][C:10](=[O:11])[C:5]=12)=[O:8])([O-:3])=[O:2].[CH:15]1(O)[CH2:19][CH2:18][CH2:17][CH2:16]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C1(C)C=CC=CC=1>[CH:15]1([N:9]2[C:10](=[O:11])[C:5]3[C:6](=[CH:12][CH:13]=[CH:14][C:4]=3[N+:1]([O-:3])=[O:2])[C:7]2=[O:8])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 117793-NitrophthalimideHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 22385744HCID 22385744, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-nitrophthalimide (3.85 g, 20.0 mmol), cyclopentanol (2.24 g, 26.0 mmol) and triphenylphosphine (6.87 g, 26.2 mmol) in tetrahydrofuran 30 ml was dropwise added 40% toluene solution (11.4 ml) of diethyl azocarboxylate under stirring in a nitrogen stream. The mixture was concentrated in vacuo, and the precipitate formed upon addition of ether was filtered off. After the filtrate was concentrated in vacuo, the residue was purified by silica gel column chromatography (hexane-ethyl acetate, 3:1) to give the title compound (3.87 g) as a colorless solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe precipitate formed upon addition of ether
  3. filtrationwas filtered off
  4. concentrationAfter the filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-34a92a00326a4334a4a06d89ecca9036
Source dataset
uspto-grants-2006_12
Patent number
US07148224B2

Reaction notes

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