O-Methylhydroxylamine hydrochloride → HCID 86707895, compound

HRID 1487314Notes

Reaction equation

HRID 1487314 reaction equation
O=[C:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:4][CH:3]1[C:17]([O:19][CH3:20])=[O:18].Cl.[CH3:22][O:23][NH2:24]>N1C=CC=CC=1>[CH3:22][O:23][N:24]=[C:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:4][CH:3]1[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 68291126HCID 68291126, compound

Product 1

HCID 86707895HCID 86707895, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-benzyl 3-methyl 4-oxopyrrolidine-1,3-dicarboxylate (12 g, 43.2 mmol) in pyridine (50 mL) at 0° C. was added O-methylhydroxylamine hydrochloride (5.51 g, 66.0 mmol) which was stirred for 10 minutes, and then it was warmed up to RT and stirred for 16 hrs. The reaction mixture was concentrated to yield a crude product which was partitioned in 300 mL of 1N HCl and 300 mL of EtOAc. The organic layer was washed with 100 mL of brine. The combined aqueous phases were extracted with 200 mL of EtOAc. The combined organic phases were dried over Na2SO4. Filtration and concentration to yield the product (12.6 g, 95% yield).

Workup

  1. stirringstirred for 16 hrs
  2. concentrationThe reaction mixture was concentrated
  3. customto yield a crude product which
  4. customwas partitioned in 300 mL of 1N HCl
  5. washThe organic layer was washed with 100 mL of brine
  6. extractionThe combined aqueous phases were extracted with 200 mL of EtOAc
  7. dry with materialThe combined organic phases were dried over Na2SO4
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-acb6638ba12e47b4a5f280f4423ef373
Source dataset
uspto-grants-2016_08
Patent number
US09428511B2

Reaction notes

Loading…