Arachidonyl azide → Arachidonyl amine

HRID 1373448Notes

Reaction equation

HRID 1373448 reaction equation
[CH2:1]([N:21]=[N+]=[N-])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C.C1COCC1>[CH2:1]([NH2:21])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 10663183Arachidonyl azide2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 10732198Arachidonyl amineYield 51%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The crude azide was reduced to the title amine as follows: To a magnetically stirred solution of 132 mg (0.43 mmol) of arachidonyl azide in 3 mL of dry diethyl ether was added 4 mL of 1.0 M solution of lithium aluminum hydride (4.0 mmol) in THF dropwise at room temperature. The reaction mixture was refluxed for 3 hours and then quenched with wet diethyl ether. The white suspension was filtered, and the filtrate was evaporated to dryness. Chromatography on silica gel (10–50% MeOH in dichloromethane) gave 65 mg (51%) of arachidonylamine as a white solid: TLC (20% EtOAc—CH2Cl2) Rf 0.33; 1H NMR (200 MHZ, CDCl3) δ5.38 (m, 8H), 2.82 (m, 6H), 2.70 (t, J=6.6 Hz, 2H), 2.08 (m, 4H), 1.40 (m, 4H), 1.26 (m, 6H), 0.89 (t, J=6.4 Hz, 3H). Anal. (C20H35N)C, H, N.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customquenched with wet diethyl ether
  3. filtrationThe white suspension was filtered
  4. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-ea01e72b907f4220854fcd517432030f
Source dataset
uspto-grants-2007_01
Patent number
US07161016B1

Reaction notes

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