Triphenylphosphine → 3-Azidocyclopentyl benzoate

HRID 1934670Notes

Reaction equation

HRID 1934670 reaction equation
[C:1]([O:9][CH:10]1[CH2:14][CH2:13][CH:12](O)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P([N:30]=[N+:31]=[N-:32])(C2C=CC=CC=2)=O)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:1]([O:9][CH:10]1[CH2:14][CH2:13][CH:12]([N:30]=[N+:31]=[N-:32])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 224676173-Hydroxycyclopentyl benzoate

Product 1

HCID 224674503-Azidocyclopentyl benzoateYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hydroxycyclopentyl benzoate (630 mg) in anhydrous tetrahydrofuran (15 mL) were added diphenylphosphoryl azide (925 mg), diethyl azodicarboxylate (585 mg) and triphenylphosphine (881 mg). After stirring for 2 hours at ambient temperature, the mixture was partitioned between ethyl acetate and water. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (10:1) to give 3-azidocyclopentyl benzoate as pale yellow oil (531 mg).

Workup

  1. customthe mixture was partitioned between ethyl acetate and water
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by a silica gel column chromatography
  6. washeluting with a mixture of hexane and ethyl acetate (10:1)

Sources & evidence

ORD record
ord-b79002d0c86746c18e99bc3bf0b69e40
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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