Hydroxyamine hydrochloride → 1-(N-Cbz-2-pyrrolidinyl)-1-buten-3-one oxime

HRID 21770Notes

Reaction equation

HRID 21770 reaction equation
[C:1]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH:16]=[CH:17][C:18](=O)[CH3:19])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+]>CO>[C:1]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH:16]=[CH:17][C:18](=[N:22][OH:23])[CH3:19])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 572702461-(N-Cbz-2-pyrrolidinyl)-1-buten-3-one

Product 1

HCID 852958861-(N-Cbz-2-pyrrolidinyl)-1-buten-3-one oximeYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of the compound from step 24e above (5.29 g, 19.3 mmol) in 30 mL of methanol were added, in small portions, 1.34 g (19.36 mmol) of hydroxylamine HCl and 1.59 g (19.36 mmol) of sodium acetate. The reaction mixture was stirred at room temperature for 1 hr, then the solvent was removed. The residue was suspended in 30 mL of water and extracted with ether. The extract was dried over Na2SO4 and concentrated to afford the title product as a syrup (5.34 g, 96% yield). IR 3328, 3030, 2880, 1685, 1444, 1415, 1303, 1181, 1115, 1021, 937 cm-1.

Workup

  1. customthe solvent was removed
  2. extractionextracted with ether
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bc4b1899a9ce4938972be6125f1539bd
Source dataset
uspto-grants-1995_06
Patent number
US05424444

Reaction notes

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