Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 86603681, compound

HRID 2376063Notes

Reaction equation

HRID 2376063 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]2[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][N:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([CH:28]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:25][CH2:26][CH3:27])=[O:24]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]2[N:16]=[CH:17][C:18](/[CH:19]=[CH:28]/[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:22]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 86603682HCID 86603682, compound

Product 1

HCID 86603681HCID 86603681, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-{[(3R)-1-benzyl-3-piperidinyl]amino}nicotinaldehyde (110 mg, 0.37 mmol) in tetrahydrofuran (4 mL) was added (carbethoxymethylene)triphenylphosphorane (260 mg, 0.75 mmol) and the mixture was stirred at ambient temperature for 18 hrs. The reaction mixture was evaporated in vacuo and the residue was partitioned between water and EtOAc. The organic layer was separated, washed water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (chloroform-MeOH=15-1) to give ethyl (2E)-3-(6-{[(3R)-1-benzyl-3-piperidinyl]amino}-3-pyridinyl)acrylate (77 mg, 57%) as an oil.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was partitioned between water and EtOAc
  3. customThe organic layer was separated
  4. washwashed water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by preparative thin layer chromatography (chloroform-MeOH=15-1)

Sources & evidence

ORD record
ord-3272724bcc5645e497040627c9aca284
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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