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

HRID 748398Notes

Reaction equation

HRID 748398 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-e182a898a0e745d8a4bf8be04cdb5a1f
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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