3-(1-Azidotridecyl)-5-trimethylsilylfuran → 3-(1-Aminotridecyl)-5-trimethylsilylfuran

HRID 488214Notes

Reaction equation

HRID 488214 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([CH:10]([C:23]1[CH:27]=[C:26]([Si:28]([CH3:31])([CH3:30])[CH3:29])[O:25][CH:24]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[N+]=[N-]>O1CCCC1>[NH2:7][CH:10]([C:23]1[CH:27]=[C:26]([Si:28]([CH3:31])([CH3:30])[CH3:29])[O:25][CH:24]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 190198473-(1-Azidotridecyl)-5-trimethylsilylfuranHCID 21226445Aluminium lithium hydride

Product 1

HCID 150370773-(1-Aminotridecyl)-5-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (a 1M solution in tetrahydrofuran; 1.1 ml, 1.1 mmol) was added dropwise to a solution of 3-(1-azidotridecyl)-5-trimethylsilylfuran (334 mg, 0.92 mmol) in tetrahydrofuran at room temperature. After one hour at room temperature, the excess hydride was destroyed by adding acetone slowly to the mixture with cooling. Sodium sulfate (ca. 0.5 g) was added and the mixture was extracted thoroughly with ethyl acetate. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by flash chromatography on silica using 5% methanol/dichloromethane containing 0.2% triethylamine. Fractions with Rf of about 0.18 on evaporation gave the title amine as a pale yellow oil.

Workup

  1. customthe excess hydride was destroyed
  2. additionby adding acetone slowly to the mixture
  3. temperaturewith cooling
  4. additionSodium sulfate (ca. 0.5 g) was added
  5. extractionthe mixture was extracted thoroughly with ethyl acetate
  6. customEvaporation of the
  7. dry with materialdried (magnesium sulfate)
  8. customextracts gave an oil, which
  9. customwas purified by flash chromatography on silica using 5% methanol/dichloromethane containing 0.2% triethylamine
  10. customFractions with Rf of about 0.18 on evaporation

Sources & evidence

ORD record
ord-e5e84b24cc6f4795b20e7cb4e14446e1
Source dataset
uspto-grants-1994_03
Patent number
US05298633

Reaction notes

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