Aluminium lithium hydride → HCID 21849492, compound

HRID 862840Notes

Reaction equation

HRID 862840 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. filtrationthe reaction mixture was filtered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-0a012f35529b4d5d849c78cf5a606597
Source dataset
uspto-grants-1998_02
Patent number
US05719176

Reaction notes

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