HCID 18705587, compound → HCID 18705581, compound

HRID 363402Notes

Reaction equation

HRID 363402 reaction equation
[NH2:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:3]([NH2:5])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:5][CH2:3][CH:2]([NH2:1])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 18705587HCID 18705587, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18705581HCID 18705581, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of 2-aminoeicosanamide prepared as in Example 28C (57.5 g, 0.176 mol) in anhydrous THF (1.0 l) under a dry argon atmosphere was added a solution of lithium aluminum hydride (880 ml--1.0M in THF, 0.880 mol) over a 30 min period. The mixture was refluxed for 17.5 h and then quenched by the dropwise addition of H2O (100 ml) while cooling in an ice bath. The solid was filtered, washed with hot THF (2×1 l) and then hot methanol (1 l). The solids were then refluxed with THF (1 l) for 15 min and filtered again. The filtrates and washings were combined and the solvent was removed in vacuo. The crude product was dissolved in THF and solid impurities were removed by filtration. The solvent was again removed in vacuo and the procedure was continued using CH2Cl2. The crude product was recrystallized from CH2Cl2 -hexane to give 37.9 g (69% yield) of the product as : mp 98°-101° C.; 1H NMR (CDCl3) δ 0.91 (t, J=6.5 Hz, 3 H), 1.33 (m, 34 H), 1.96 (br s, 4 H), 2.52 (m, 1 H), 2.78 (m, 2 H).

Workup

  1. temperatureThe mixture was refluxed for 17.5 h
  2. customquenched by the dropwise addition of H2O (100 ml)
  3. temperaturewhile cooling in an ice bath
  4. filtrationThe solid was filtered
  5. washwashed with hot THF (2×1 l)
  6. temperatureThe solids were then refluxed with THF (1 l) for 15 min
  7. filtrationfiltered again
  8. customthe solvent was removed in vacuo
  9. dissolutionThe crude product was dissolved in THF
  10. customsolid impurities were removed by filtration
  11. customThe solvent was again removed in vacuo
  12. customThe crude product was recrystallized from CH2Cl2 -hexane

Sources & evidence

ORD record
ord-23561e3879394480b551761445a8b1fd
Source dataset
uspto-grants-1999_02
Patent number
US05874421

Reaction notes

Loading…