Water → Ethyl 3-(1-isopropylpiperidin-4-yl)acrylate

HRID 491833Notes

Reaction equation

HRID 491833 reaction equation
[H-].[Na+].[CH:3]([N:6]1[CH2:11][CH2:10][CH:9]([CH:12]=O)[CH2:8][CH2:7]1)([CH3:5])[CH3:4].[OH2:14].[O:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>C(OCC)C>[CH:3]([N:6]1[CH2:7][CH2:8][CH:9]([CH:12]=[CH:17][C:16]([O:15][CH2:19][CH3:18])=[O:14])[CH2:10][CH2:11]1)([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 178939231-Isopropyl-piperidine-4-carboxaldehyde

Product 1

HCID 68453328Ethyl 3-(1-isopropylpiperidin-4-yl)acrylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Triethyl phosphonoacetate (7.96 g) is dissolved in tetrahydrofuran (50 ml) and thereto is added gradually 60% sodium hydride in oil (1.45 g) under ice-cooling. After stirring for 20 minutes under ice-cooling, to the mixture is added 1-isopropylpiperidine-4-carbaldehyde (5.03 g) obtained in Reference Example 134(2) in tetrahydrofuran (25 ml). The reaction solution is stirred for 3 hours, diluted with diethyl ether, thereto is added water and the mixture is extracted with ethyl acetate. The organic layer is washed with water and saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1) to give ethyl 3-(1-isopropylpiperidin-4-yl)acrylate (6.87 g).

Workup

  1. temperaturecooling
  2. temperaturecooling, to the mixture
  3. stirringThe reaction solution is stirred for 3 hours
  4. extractionthe mixture is extracted with ethyl acetate
  5. washThe organic layer is washed with water and saturated brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto remove the solvent under reduced pressure
  9. customThe resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-8f1065fd9fc54dbc8246f8d59beac4ef
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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