Ethanol → 5-(Cyclopentylmethyl)isoxazol-3-amine

HRID 1353122Notes

Reaction equation

HRID 1353122 reaction equation
Cl.[NH2:2][OH:3].[CH:4]1([CH2:9][C:10]#[C:11][C:12]#[N:13])[CH2:8][CH2:7][CH2:6][CH2:5]1.CCO>[OH-].[Na+].CCOCC>[CH:4]1([CH2:9][C:10]2[O:3][N:2]=[C:12]([NH2:13])[CH:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 211023174-Cyclopentyl-but-2-ynenitrile

Product 1

HCID 211023185-(Cyclopentylmethyl)isoxazol-3-amine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

Hydroxylamine HCl (20.3 mmol) was dissolved in 14.9 mL of 2.5 M aqueous NaOH solution at rt and 4-Cyclopentyl-but-2-ynenitrile (16.9 mmol) was added in solution with 50 mL EtOH. The cloudy suspension was stirred at rt for 2 hours. The reaction material was then diluted with 200 mL of Et2O and washed with two 50 mL portions of water, followed by 50 mL of aqueous saturated sodium chloride solution. The organics were then dried over Na2SO4, filtered and concentrated under reduced pressure. The crude products were then purified through flash chromatography to give 5-Cyclopentylmethyl-isoxazol-3-ylamine.

Workup

  1. washwashed with two 50 mL portions of water
  2. dry with materialThe organics were then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude products were then purified through flash chromatography

Sources & evidence

ORD record
ord-f6b19d36c59f48349f80695fbf01ca14
Source dataset
uspto-grants-2007_05
Patent number
US07220865B2

Reaction notes

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