1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(Trimethylsilyl)ethyl 5-(2-pyridyl)valerate

HRID 499580Notes

Reaction equation

HRID 499580 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12].[CH3:14][Si:15]([CH:18](O)[CH3:19])([CH3:17])[CH3:16].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:19][CH2:18][Si:15]([CH3:17])([CH3:16])[CH3:14])=[O:12]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 112523245-pyridin-2-ylpentanoic AcidHCID 124478981-(Trimethylsilyl)ethanol

Product 1

HCID 229393742-(Trimethylsilyl)ethyl 5-(2-pyridyl)valerateYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(2-Pyridyl)valeric acid (1.5 g, 8.4 mmol) was dissolved in N,N-dimethylformamide (25 ml), and trimethylsilylethanol (2.0 g, 16.7 mmol), WSC (3.2 g, 16.7 mmol) and HOBt (2.3 g, 16.7 mmol) were added thereto successively. The mixture was stirred at room temperature for 6 hrs. The solvent was evaporated, and the residue was combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel (60 g) column chromatography. The fractions eluted with hexane-ethyl acetate (2:1, v/v) were collected and concentrated to give the titled compound (1.1 g, 49%).

Workup

  1. customThe solvent was evaporated
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. washThe fractions eluted with hexane-ethyl acetate (2:1
  6. customv/v) were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-89ada5bf13c6403ca15e3bb0ad9b7e01
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

Loading…