Triphenylphosphine → ethyl 5-{(2RS,3RS)-3-amino-2-(4-nitrophenyl)butyl}-2-furancarboxylate

HRID 1602574Notes

Reaction equation

HRID 1602574 reaction equation
O[CH:2]([CH3:24])[CH:3]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[CH2:4][C:5]1[O:9][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][CH:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:44](C(OCC)=O)=NC(OCC)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[NH2:44][CH:2]([CH3:24])[CH:3]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[CH2:4][C:5]1[O:9][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19364506ethyl 5-{(2RS,3SR)-3-hydroxy-2-(4-nitrophenyl)butyl}-2-furancarboxylate

Product 1

HCID 53734556ethyl 5-{(2RS,3RS)-3-amino-2-(4-nitrophenyl)butyl}-2-furancarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.66 g of ethyl 5-{(2RS,3SR)-3-hydroxy-2-(4-nitrophenyl)butyl}-2-furancarboxylate in 40 ml of tetrahydrofuran was mixed with 4.32 g of triphenylphosphine, 2.60 ml of diethyl azodicarboxylate and 4.53 g of diphenylphosphoryl azide under cooling with ice under stirring and stirred at room temperature for 18 hours. The reaction solution was evaporated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography [hexane/ethyl acetate=50/1→30/1]. The resulting azide was refluxed together with 2.37 g of triphenylphosphine in 55 ml of 10% hydrous tetrahydrofuran under heating for 6 hours. The reaction solution was cooled to room temperature, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [ethylene chloride/methanol=100/1→20/1] to give 2.89 g of the title compound as a yellow oily substance.

Workup

  1. temperatureunder cooling with ice
  2. stirringstirred at room temperature for 18 hours
  3. customThe reaction solution was evaporated to dryness under reduced pressure
  4. customthe residue was purified by silica gel column chromatography [hexane/ethyl acetate=50/1→30/1]
  5. temperatureThe resulting azide was refluxed together with 2.37 g of triphenylphosphine in 55 ml of 10% hydrous tetrahydrofuran
  6. temperatureunder heating for 6 hours
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography [ethylene chloride/methanol=100/1→20/1]

Sources & evidence

ORD record
ord-e15ff9b65b464e289f0cb9f647275f87
Source dataset
uspto-grants-1999_11
Patent number
US05981573

Reaction notes

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