Benzyloxyamine hydrochloride → 1-(Benzyloxyimino-methyl)-cyclopentanecarboxylic acid methyl ester

HRID 2055165Notes

Reaction equation

HRID 2055165 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH:10]=O)[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].C([O-])(=O)C.[Na+].Cl.[CH2:18]([O:25][NH2:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CO>[CH3:1][O:2][C:3]([C:5]1([CH:10]=[N:26][O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6][CH2:7][CH2:8][CH2:9]1)=[O:4]

Participants

5

Reactant 3

HCID 102312Benzyloxyamine hydrochlorideHCID 517045Sodium AcetateHCID 10931680Methyl 1-formylcyclopentanecarboxylate

Product 1

HCID 866064701-(Benzyloxyimino-methyl)-cyclopentanecarboxylic acid methyl esterYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-formyl-cyclopentanecarboxylic acid methyl ester (3.1 g, 19.8 mmol), sodium acetate (2.74 g, 39.72 mmol) and O-benzylhydroxylamine hydrochloride (6.34 g, 39.7 mmol) were stirred in methanol (120 mL) for 18 h. The methanol was removed in vacuo and the residue partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc (50 mL×2). The combined organic extracts were dried (MgSO4) and were evaporated in vacuo. Purification by flash column chromatography using an eluting system of hexane/EtOAc (95:5 to 90:10) provided the title compound as a clear colorless oil (2.26 g, 44%). MH+262.

Workup

  1. customThe methanol was removed in vacuo
  2. customthe residue partitioned between water and EtOAc
  3. extractionThe aqueous phase was extracted with EtOAc (50 mL×2)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customwere evaporated in vacuo
  6. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-0ba7c710b4a0491bb33e3f5043ea4866
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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