Acetic Acid → HCID 86669073, compound

HRID 1807397Notes

Reaction equation

HRID 1807397 reaction equation
[CH3:1][O:2][N:3]=[C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[C:14]([Cl:15])=[CH:13][C:12]([Cl:16])=[CH:11][C:10]=1[Cl:17])[CH3:5].C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[Cl:15][C:14]1[CH:13]=[C:12]([Cl:16])[CH:11]=[C:10]([Cl:17])[C:9]=1[C@@H:7]1[CH2:8][C@H:6]1[CH:4]([NH:3][O:2][CH3:1])[CH3:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 86669074HCID 86669074, compound

Product 1

HCID 86669073HCID 86669073, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-[2-(2,4,6-trichloro-phenyl)-cyclopropyl]-ethanone O-methyl-oxime (0.19 mmol), prepared as described in example P23, in ethanol (1 ml) and acetic acid (1 ml) was treated at ambient temperature with sodium cyanoborohydride (200 mg, 3.18 mmol) added in one portion. The resulting solution was stirred at ambient temperature for 20 hours. The solvent was evaporated under reduced pressure (co-evaporation with toluene twice) and the residue was slurried with 1 M NaOH (5 ml). The aqueous phase was extracted with ether (3×10 ml), washed with brine and dried over anhydrous Na2SO4. After removal of the solvent, the residue was purified by flash chromatography over silica gel (5 g) (eluent: c-hexane/ethyl acetate 5:1). 25 mg (45.0% of theory) of trans-N-{1-[2-(2,4,6-trichlorophenyl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine as a mixture of diastereomeres was obtained in form of a clear liquid.

Workup

  1. additionadded in one portion
  2. customThe solvent was evaporated under reduced pressure (co-evaporation with toluene twice) and the residue
  3. extractionThe aqueous phase was extracted with ether (3×10 ml)
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customAfter removal of the solvent
  7. customthe residue was purified by flash chromatography over silica gel (5 g) (eluent: c-hexane/ethyl acetate 5:1)
  8. addition25 mg (45.0% of theory) of trans-N-{1-[2-(2,4,6-trichlorophenyl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine as a mixture of diastereomeres
  9. customwas obtained in form of a clear liquid

Sources & evidence

ORD record
ord-599d3c10d0bd4760b7f5142134c67347
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Reaction notes

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