Tetrahydrofuran → HCID 14986683, compound

HRID 465587Notes

Reaction equation

HRID 465587 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH2:17])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:24]1CCC[CH2:25]1>>[NH2:17][CH2:15][CH2:14][CH2:13][CH2:12][CH:11]([CH2:10][CH2:9][CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:25][OH:24]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 19874775HCID 19874775, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14986683HCID 14986683, compound

Procedure

A solution of 1.0 g (3.17 mmol) of 5-[3-(tetrahydropyranyloxy)propyl]valeramide in 5 ml tetrahydrofuran is added dropwise to a suspension of 0.481 g (12.68 mmol) lithium aluminium hydride in 20 ml dry tetrahydrofuran. The reaction mixture is refluxed for 2.5 h, cooled in an ice-bath and quenched by the addition of 0.5 ml water, 0.5 ml 15% aqueous sodium hydroxide followed by 1.5 ml water. The mixture is stirred for 15 min and filtered, washed and then subjected to evaporation to give 6-amino-2-[3-(tetrahydropyranyloxy)propyl]-hexan-1-ol.

Workup

  1. temperatureThe reaction mixture is refluxed for 2.5 h
  2. temperaturecooled in an ice-bath
  3. customquenched by the addition of 0.5 ml water, 0.5 ml 15% aqueous sodium hydroxide
  4. filtrationfiltered
  5. washwashed
  6. customsubjected to evaporation

Sources & evidence

ORD record
ord-b447f73ef61d411bbb15ca58c13f7548
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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