Triphenylphosphine → HCID 69310479, compound

HRID 750919Notes

Reaction equation

HRID 750919 reaction equation
[C:1]([CH:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:20][C@@H:19]([CH2:21][N:22]=[N+]=[N-])[O:18][C:17]3=[O:25])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O>[C:1]([CH:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([N:16]3[CH2:20][C@H:19]([CH2:21][NH2:22])[O:18][C:17]3=[O:25])=[CH:14][CH:15]=2)[CH2:6][CH2:5]1)#[N:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86591703HCID 86591703, compound

Product 1

HCID 69310479HCID 69310479, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of (S)-{3-[4-(4-cyanomethylidene-piperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-azide (2.94 mmol), triphenylphosphine (3.81 mmol) was stirred for 3 hours. It was refluxed by adding water overnight. Removal of solvent and purification of the product on silica gel column chromatography provided (S)-{3-[4-(4-cyanomethylidene-piperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-amine in 71% yield.

Workup

  1. temperatureIt was refluxed
  2. customRemoval of solvent and purification of the product on silica gel column chromatography

Sources & evidence

ORD record
ord-4b87edd3d18845a890ec380810a092c0
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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