Triphenylphosphine → HCID 57976112, compound

HRID 1865189Notes

Reaction equation

HRID 1865189 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH3:12][O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH:19](O)[CH2:18][CH2:17]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:12][O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6](=[O:11])[CH2:5]3)[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 769555-HydroxyoxindoleHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 213537524-Piperidinol, 1-(2-methoxyethyl)- (9CI)

Product 1

HCID 57976112HCID 57976112, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an oven dried, nitrogen flushed 100 ml round bottom flask was added 5-hydroxyoxindole (10 mmol), 1-(2-methoxyethyl)-piperidin-4-ol (11 mmol), triphenylphosphine (15 mmol), Anhydrous tetrahydrofuran (35 ml) and a stirrer bar. Diethyl azodicarboxylate (15 mmol) was added slowly to the mixture and stirred at room temperature overnight. The reaction was concentrated in vacuo and flash chromatography (silica, 5% methanol in ethyl acetate). Upon concentration a reddish oil (470 mg) was obtained with a 75% purity by H-NMR and LC/MS.

Workup

  1. customTo an oven dried
  2. customnitrogen flushed 100 ml round bottom flask
  3. concentrationThe reaction was concentrated in vacuo and flash chromatography (silica, 5% methanol in ethyl acetate)
  4. concentrationUpon concentration a reddish oil (470 mg)
  5. customwas obtained with a 75% purity by H-NMR and LC/MS

Sources & evidence

ORD record
ord-1414e520ff8249cf8404257d3b4433ab
Source dataset
uspto-grants-2009_12
Patent number
US07626031B2

Reaction notes

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