Triphenylphosphine → HCID 60029919, compound

HRID 496417Notes

Reaction equation

HRID 496417 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[CH2:13][N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24].[N:25]1([CH2:30][CH:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)O)[CH:29]=[CH:28][N:27]=[CH:26]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.CO.C(Cl)Cl>[N:25]1([CH2:30][C@H:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:1][C:2]2[CH:11]=[CH:10][C:9]3[C:8](=[O:12])[CH2:7][CH2:6][CH2:5][C:4]=3[C:3]=2[CH2:13][N:14]2[C:15](=[O:24])[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]2=[O:23])[CH:29]=[CH:28][N:27]=[CH:26]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 322392-(1H-imidazol-1-yl)-1-phenylethanolHCID 5462977Diethyl azodicarboxylateHCID 22324865HCID 22324865, compound

Product 1

HCID 60029919HCID 60029919, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a slurry of 2-(2-Hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl)-isoindole-1,3-dione (862 mg, 2.68 mmol) in THF (17 mL) was added ®-2-imidazol-1-yl-1-phenyl-ethanol (606 mg, 3.22 mmol) and triphenylphospine (846 mg, 3.22 mmol). After 15 min, diethylazodicarboxylate (0.51 mL, 3.22 mmol) was added and the reaction became homogenous. The reaction was stirred for 2 days and concentrated to give a reddish-brown foam. Purification by chromatography (10-20% acetone/CH2Cl2 then 5% MeOH/CH2Cl2) afforded the title compound as a light brown foam (1.15 g, 2.35 mmol, 87%). The structure was confirmed by NMR and mass spectrometry. MS m/z 492 (M++H).

Workup

  1. concentrationconcentrated
  2. customto give a reddish-brown foam
  3. customPurification by chromatography (10-20% acetone/CH2Cl2

Sources & evidence

ORD record
ord-9471ddd56bcd4969b2b044abea5c792a
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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