Hydroxyamine hydrochloride → HCID 57827570, compound

HRID 1693180Notes

Reaction equation

HRID 1693180 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[CH2:9]([O:12][C@@H:13]([CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:14][CH:15]=O)[CH:10]=[CH2:11].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O.C(O)C>[CH2:9]([O:12][C@@H:13]([CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:14][CH:15]=[N:2][OH:3])[CH:10]=[CH2:11]

Participants

8

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 57827637HCID 57827637, compound

Product 1

HCID 57827570HCID 57827570, compoundYield 53.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (5.14 g) and methyl iodide (4.90 mL) were added to a mixed solution of 2-((R)-2-allyloxy-3-benzyloxy-propyl)-[1,3]dithiane (12 g) in acetonitrile (27 mL) and water (4.5 mL), and then the mixture was stirred at 40° C. After four hours, water (3 mL) and methyl iodide (2 mL) were added to the reaction solution. After further three hours, methyl iodide (1 mL) was added to the reaction solution. After stirring for eight hours in total, water and t-butyl methyl ether were added to the reaction solution, and the organic layer was separated. The organic layer was washed with brine. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to obtain crude (R)-3-allyloxy-4-benzyloxy-butyraldehyde (about 10 g). The crude product was used for the next reaction without further purification. Hydroxylamine hydrochloride (4.29 g) and sodium acetate (4.92 g) were sequentially added to a solution of ethanol (60 mL) and water (15 mL). The above aldehyde (10 g) was added to the mixture, followed by stirring for 20 hours. A saturated sodium bicarbonate solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and then the filtrate was concentrated under reduced pressure to obtain a residue. The residue was subjected to silica gel column chromatography to obtain the title compound (5.74 g).

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto obtain a residue

Sources & evidence

ORD record
ord-41e594df2bb0418bafd72d2483f22d6b
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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