Triphenylphosphine → HCID 69146214, compound

HRID 746997Notes

Reaction equation

HRID 746997 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][C:26]([CH:31]([OH:34])[CH2:32][OH:33])([CH2:29]O)[CH2:25][CH2:24]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][C:26]2([CH2:29][O:33][CH2:32][CH:31]2[OH:34])[CH2:25][CH2:24]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 69146242HCID 69146242, compound

Product 1

HCID 69146214HCID 69146214, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (1.4 g, 8.1 mmol) was added to a solution of 4-(1,2-dihydroxyethyl)-4-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester (Description 3; 2 g, 6.5 mmol) and triphenylphosphine (2.4 g, 9.1 mmol) in tetrahydrofuran (40 ml). The reaction was stirred at room temperature for 2 hours then the solvent was removed in vacuo. The residue was purified by flash column chromatography on silica, eluting with 1, 2 and 4% methanol/dichloromethane, to give the title compound (1.43 g, 76%).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by flash column chromatography on silica
  3. washeluting with 1, 2 and 4% methanol/dichloromethane

Sources & evidence

ORD record
ord-25247a99d66c480f9ee1fc4b413ffedb
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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