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

HRID 850660Notes

Reaction equation

HRID 850660 reaction equation
[N:1]([CH:4]([CH3:26])[CH:5]([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)[CH2:6][C:7]1[O:11][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C>O1CCCC1.O>[NH2:1][CH:4]([CH3:26])[CH:5]([C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)[CH2:6][C:7]1[O:11][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 54125754ethyl 5-{(2RS,3RS)-3-azido-2-(4-nitrophenyl)butyl}-2-furancarboxylate

Product 1

HCID 53734556ethyl 5-{(2RS,3RS)-3-amino-2-(4-nitrophenyl)butyl}-2-furancarboxylateYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3.24 g of ethyl 5-{(2RS,3RS)-3-azido-2-(4-nitrophenyl)butyl}-2-furancarboxylate was dissolved in a mixed solution of 50 ml of tetrahydrofuran and 5 ml of water, and 2.37 g of triphenylphosphine was added thereto, followed by heating and refluxing or 6 hours. The reaction solution was left to cool to room temperature, and then ethyl ether and water were added thereto for extraction. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1→20/1) to obtain 2.89 g of the above-identified compound.

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperaturerefluxing or 6 hours
  4. waitThe reaction solution was left
  5. extractionfor extraction
  6. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe drying agent was filtered off
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1→20/1)

Sources & evidence

ORD record
ord-03db5212398e4b218c6a66409d617747
Source dataset
uspto-grants-2000_01
Patent number
US06017956

Reaction notes

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