Benzyloxyamine hydrochloride → HCID 86606483, compound

HRID 2055197Notes

Reaction equation

HRID 2055197 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH:13]=O)[CH2:10][C@H:9]([CH3:11])[CH2:8][C@H:7]([CH3:12])[CH2:6]1)=[O:4].C([O-])(=O)C.[Na+].Cl.[CH2:21]([O:28][NH2:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO>[CH3:1][O:2][C:3]([C:5]1([CH:13]=[N:29][O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:6][C@H:7]([CH3:12])[CH2:8][C@H:9]([CH3:11])[CH2:10]1)=[O:4]

Participants

5

Reactant 3

HCID 102312Benzyloxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86606481HCID 86606481, compound

Product 1

HCID 86606483HCID 86606483, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (3S,5R)-1-formyl-3,5-dimethyl-cyclohexanecarboxylic acid methyl ester (5.5 g, 27.8 mmol), sodium acetate (4.57 g, 55.6 mmol) and O-benzylhydroxylamine hydrochloride (8.88 g, 55.6 mmol) were stirred in methanol (100 mL) for 18 h. The methanol was removed in vacuo, water (100 mL) was added and the aqueous phase was extracted with EtOAc (50 mL×5). The combined organic extracts were dried (MgSO4) and were evaporated in vacuo. The residue was purified by flash column chromatography using an eluting system of hexane/EtOAc (99:1) to yield the title compound as a clear yellow oil (4.8 g, 57%). MH+304.

Workup

  1. customThe methanol was removed in vacuo, water (100 mL)
  2. additionwas added
  3. extractionthe aqueous phase was extracted with EtOAc (50 mL×5)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customwere evaporated in vacuo
  6. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-f905118b3eaa47159fd2fd3eefe24f5f
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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