Triphenylphosphine → HCID 57137509, compound

HRID 1636844Notes

Reaction equation

HRID 1636844 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]#[N:13])=[CH:9]2)=[CH:4][CH:3]=1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([CH:34]([P:36]([O:41][CH2:42][CH3:43])([O:38][CH2:39][CH3:40])=[O:37])O)=[CH:30][CH:29]=2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>O1CCCC1>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([O:27][C:28]2[CH:29]=[CH:30][C:31]([CH:34]([O:1][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][C:8]([C:12]#[N:13])=[CH:7][CH:6]=4)[CH:11]=3)[P:36]([O:38][CH2:39][CH3:40])([O:41][CH2:42][CH3:43])=[O:37])=[CH:32][CH:33]=2)[CH2:23][CH2:22]1)=[O:20])([CH3:16])([CH3:17])[CH3:15]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 222436217-Hydroxynaphthalene-2-carbonitrileHCID 86755217HCID 86755217, compound

Product 1

HCID 57137509HCID 57137509, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.50 g (0.0088 mol) 7-hydroxy-naphthalene-2-carbonitrile, 3.93 g (0.0088 mol) 4-{4-[(diethoxy-phosphoryl)-hydroxy-methyl]-phenoxy}-piperidine-1-carboxylic acid tert.-butyl ester and 3.73 g (0.0142 mol) triphenylphosphine in 150 ml tetrahydrofuran is admixed at 5° C. with 2.23 ml (0.0142 mol) azodicarboxylic acid diethyl ester and stirred for 96 h at room temperature. After concentration the residue is purified by chromatography on a silica gel column (mobile solvent: ethyl acetate/methanol 19:1). After concentrating the appropriate column fractions one obtains 2.47 g (47%) of the title compound as a viscous, yellow oil. 31P-NMR: δ=19.0 ppm.

Workup

  1. concentrationAfter concentration the residue
  2. customis purified by chromatography on a silica gel column (mobile solvent: ethyl acetate/methanol 19:1)
  3. concentrationAfter concentrating the appropriate column fractions one

Sources & evidence

ORD record
ord-08bfa52fdd614ff3998e833cd9df2d47
Source dataset
uspto-grants-2000_03
Patent number
US06037334

Reaction notes

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