Ethanol → HCID 59134550, compound

HRID 1993501Notes

Reaction equation

HRID 1993501 reaction equation
[CH2:1]([N:8]1[CH2:14][CH:13]2[C:15](=O)[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.Cl.[NH2:21][OH:22]>N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:14][CH:13]2[C:15](=[N:21][OH:22])[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 156391343-Benzyl-3-azabicyclo(3.2.1)octan-8-one

Product 1

HCID 59134550HCID 59134550, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of 19 g (88 mmole) of 3-benzyl-3-azabicyclo[3.2.1]octan-8-one (J. Med. Chem. 1994, 37, 2831), 200 ml of ethanol, 8.78 g (126.4 mmole) of hydroxylamine hydrochloride and 13 ml of pyridine are heated and stirred on a 100° C. oil-bath, then the mixture is evaporated. To the residue 65 ml of 2.5 N sodium hydroxide solution is added, the resulting solution is extracted with 3×120 ml of ethyl acetate. The extractum is dried over sodium sulphate and evaporated. The resulting oil is purified by column chromatography (n-hexane-ethyl acetate from 9:1 to 1:1) to obtain 11.05 g (54%) of white, crystalline material. M.p.: 92-95° C. (MH+)=231.

Workup

  1. temperatureare heated
  2. customthe mixture is evaporated
  3. additionTo the residue 65 ml of 2.5 N sodium hydroxide solution is added
  4. extractionthe resulting solution is extracted with 3×120 ml of ethyl acetate
  5. dry with materialThe extractum is dried over sodium sulphate
  6. customevaporated
  7. customThe resulting oil is purified by column chromatography (n-hexane-ethyl acetate from 9:1 to 1:1)
  8. customto obtain 11.05 g (54%) of white, crystalline material

Sources & evidence

ORD record
ord-8f0e68926f9e4cf1965df81f92ebbc16
Source dataset
uspto-grants-2010_01
Patent number
US07652021B2

Reaction notes

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