Aluminium lithium hydride → HCID 68299260, compound

HRID 1844659Notes

Reaction equation

HRID 1844659 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([O:12][CH3:13])[CH2:8][CH2:7]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:13][O:12][N:9]1[CH2:10][CH2:11][CH:6]([CH2:5][CH2:4][OH:3])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68299228HCID 68299228, compound

Product 1

HCID 68299260HCID 68299260, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (1-methoxy-piperidin-4-yl)-acetic acid ethyl ester (16.7 g, 83 mmol) in 50 ml of THF was added dropwise to a suspension of lithium aluminum hydride (6.3 g, 166 mmol) in 150 ml of THF at 0° C. under nitrogen. After the addition, the mixture was warmed to room temperature for 2 h. Then, the resulting mixture was poured into 500 ml of ice water and extracted with CH2Cl2 three times. The combined organic layers were dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel. Yield: 12.0 g of 2-(1-methoxy-piperidin-4-yl)-ethanol as an oil.

Workup

  1. additionAfter the addition
  2. extractionextracted with CH2Cl2 three times
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2e4d5b4efa484fd59af8248e253d85e7
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

Loading…