HCID 14986682, compound → HCID 14986683, compound

HRID 1494128Notes

Reaction equation

HRID 1494128 reaction equation
[C:1]([CH:6]([CH2:13][CH2:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1)[CH2:7][CH2:8][CH2:9][C:10]([NH2:12])=O)(OCC)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:12][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]([CH2:13][CH2:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1)[CH2:1][OH:2]

Participants

4

Reactant 2

HCID 14986682HCID 14986682, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14986683HCID 14986683, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.0 g (3.17 mmol) of 5-carbethoxy-5-[3-(tetrahydropyranyloxy)propyl]-valeramide in 5 mL tetrahydrofuran is added dropwise to a suspension of 0.481 g (12.68 mmol) lithium aluminum hydride in 20 mL dry tetrahydrofuran. The reaction is refluxed for 21/2 hours, cooled in an ice-bath and quenched by the addition of 0.5 mL water, 0.5 mL 15% sodium hydroxide followed by 1.5 mL water. The mixture is stirred for 15 minutes and filtered, washed and then subjected to evaporation to give 6-amino-2-[3-(tetrahydropyranyloxy)-propyl]hexan-1-ol.

Workup

  1. temperatureThe reaction is refluxed for 21/2 hours
  2. temperaturecooled in an ice-bath
  3. customquenched by the addition of 0.5 mL water, 0.5 mL 15% sodium hydroxide
  4. filtrationfiltered
  5. washwashed
  6. customsubjected to evaporation

Sources & evidence

ORD record
ord-0e80d5e6423349f89af9c4ccda888e52
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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