Aluminium lithium hydride → HCID 21849492, compound

HRID 1451603Notes

Reaction equation

HRID 1451603 reaction equation
C([O:4][CH2:5][C:6]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])([NH:12][C:13](=O)[CH2:14][CH2:15][CH2:16][CH3:17])[CH2:7][O:8]C(=O)C)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH2:19]([C:6]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])([CH2:5][OH:4])[CH2:7][OH:8])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21849166HCID 21849166, compound

Product 1

HCID 21849492HCID 21849492, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1,3-Diacetoxy-2-octadecyl-2-(N-pentanoylamino)propane (400 mg) was dissolved in 30 ml of dry ether and 150 mg of lithium aluminum hydride was added thereto under ice-cooling. The mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated and 20 ml of dry tetrahydrofuran was added thereto. Under ice-cooling, 0.15 ml of water, 0.15 ml of a 15% aqueous sodium hydroxide solution and 0.45 ml of water were added in order and the reaction mixture was filtered. The filtrate was concentrated and purified by silica gel column chromatography using chloroform-methanol-acetic acid (19:1:0.1→10:1:0.05) as an eluent to give 153 mg of colorless, powdery 2-octadecyl-2-(N-pentylamino)-1,3-propanediol.

Workup

  1. temperatureunder ice-cooling
  2. concentrationThe reaction mixture was concentrated
  3. addition20 ml of dry tetrahydrofuran was added
  4. temperatureUnder ice-cooling
  5. addition0.15 ml of water, 0.15 ml of a 15% aqueous sodium hydroxide solution and 0.45 ml of water were added in order
  6. filtrationthe reaction mixture was filtered
  7. concentrationThe filtrate was concentrated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b5190292c719495fbf24dab0ccf6470d
Source dataset
uspto-grants-1997_02
Patent number
US05604229

Reaction notes

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