Triphenylphosphine → HCID 19038072, compound

HRID 263453Notes

Reaction equation

HRID 263453 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[Cl:32][C:33]1[C:34]([OH:39])=[N:35][O:36][C:37]=1[CH3:38].O[CH:41]1[CH:46]2[CH2:47][CH2:48][N:43]([CH2:44][CH2:45]2)[CH2:42]1>O1CCCC1>[Cl:32][C:33]1[C:34]([O:39][CH:41]2[CH:46]3[CH2:47][CH2:48][N:43]([CH2:44][CH2:45]3)[CH2:42]2)=[N:35][O:36][C:37]=1[CH3:38]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 15381(+-)-3-QuinuclidinolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178435011HCID 178435011, compound

Product 1

HCID 19038072HCID 19038072, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7.86 g of triphenylphosphine in 100 ml of tetrahydrofuran was cooled to 5° C., and then 5.22 g of diethyl azodicarboxylate were added dropwise to the cooled solution, followed by 4.00 g of 4-chloro-3-hydroxy-5-methylisoxazole. 3.81 g of 3-hydroxyquinuclidine were then added to the resulting mixture, and the mixture was stirred at room temperature for 24 hours. At the end of this time, the solvent was removed from the mixture by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using ethyl acetate as the eluent, to afford 4.72 g (yield 64.8%) of the title compound as a colorless powder, melting at 37°-38° C.

Workup

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

Sources & evidence

ORD record
ord-8d327ad29bfb4df2a33cd8e0be43ddb6
Source dataset
uspto-grants-1997_07
Patent number
US05643923

Reaction notes

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