Triphenylphosphine → HCID 86607287, compound

HRID 226002Notes

Reaction equation

HRID 226002 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH:18]=[CH2:19])[CH:13](O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1C=CC(P([N:66]=[N+:67]=[N-:68])(C2C=CC=CC=2)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH:18]=[CH2:19])[CH:13]([N:66]=[N+:67]=[N-:68])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68827811HCID 68827811, compound

Product 1

HCID 86607287HCID 86607287, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 4-Allyl-3-hydroxy-piperidine-1-carboxylic acid benzyl ester (293 mg, 1.06 mmol) were added triphenyl phosphine(362 mg, 1.38 mmol), a solution of diethyl azodicarboxylate in toluene (0.6 ml, 1.38 immol; 40% solution) and DPPA (297 μL, 1.38 mmol). After stirring for 4 h, the mixture was evaporated and the residue was purified by column chromatography (15% AcOEt-hexane)to give 4-Allyl-3-azido-piperidine-1-carboxylic acid benzyl ester.

Workup

  1. customthe mixture was evaporated
  2. customthe residue was purified by column chromatography (15% AcOEt-hexane)

Sources & evidence

ORD record
ord-44f62470f85d4c8783733509fbef13cf
Source dataset
uspto-grants-2009_07
Patent number
US07557110B2

Reaction notes

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