Triphenylphosphine → 3-(3-Quinuclidinyloxy)isoxazole

HRID 263454Notes

Reaction equation

HRID 263454 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][C:33]1[CH:37]=[CH:36][O:35][N:34]=1.O[CH:39]1[CH:44]2[CH2:45][CH2:46][N:41]([CH2:42][CH2:43]2)[CH2:40]1>O1CCCC1>[N:41]12[CH2:46][CH2:45][CH:44]([CH2:43][CH2:42]1)[CH:39]([O:32][C:33]1[CH:37]=[CH:36][O:35][N:34]=1)[CH2:40]2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 15381(+-)-3-QuinuclidinolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178516613HCID 178516613, compound

Product 1

HCID 101980493-(3-Quinuclidinyloxy)isoxazoleYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 9.18 g of triphenylphosphine in 100 ml of tetrahydrofuran was cooled to 5° C. 6.10 g of diethyl azodicarboxylate were then added dropwise to the cooled solution, after which 2.98 g of 3-hydroxyisoxazole and 4.45 g of 3-hydroxyquinuclidine were added, and the resulting mixture was stirred at room temperature for 24 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using ethyl acetate as the eluent, to afford 5.18 g (yield 76.2%) of the title compound as a colorless powder, melting at 80°-81° C.

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. customthe resulting residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-45a5c665ce2f43eeabe63b686c57eea9
Source dataset
uspto-grants-1997_07
Patent number
US05643923

Reaction notes

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