O-methylhydroxylammonium chloride → 1-(t-Butoxycarbonyl)-3-methoxyiminopyrrolidine

HRID 622448Notes

Reaction equation

HRID 622448 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10](=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][O:15][NH3+:16].[Cl-]>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10](=[N:16][O:15][CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11639O-methylhydroxylammonium chlorideHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylate

Product 1

HCID 536718421-(t-Butoxycarbonyl)-3-methoxyiminopyrrolidineYield 99.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

27 ml of anhydrous pyridine were added to a mixture of 2.0 g of 1-(t-butoxycarbonyl)-3-pyrrolidone and 992 mg of o-methylhydroxylamine hydrochloride, and the mixture was kept stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off and saturated aqueous sodium bicarbonate solution was added to the residue until it was basic. The mixture was extracted with chloroform, and the extract was dried over anhydrous magnesium sulfate and concentrated. The residue was chromatographed over silica gel, using a 3/1 mixture of benzene and ethyl acetate as eluent, giving 2.3 g of 1-(t-butoxycarbonyl)-3-methoxyiminopyrrolidine as a mixture of syn- and anti-isomers.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionsaturated aqueous sodium bicarbonate solution was added to the residue until it
  4. extractionThe mixture was extracted with chloroform
  5. dry with materialthe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed over silica gel
  8. additiona 3/1 mixture of benzene and ethyl acetate as eluent

Sources & evidence

ORD record
ord-e04649028fca4921b1df1eafdc9702eb
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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