Acetic Acid → HCID 86669071, compound

HRID 1807396Notes

Reaction equation

HRID 1807396 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][CH:12]=[CH:11][C:10]=1[Cl:16])[CH3:5].C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[Cl:15][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:16])[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 86669072HCID 86669072, compound

Product 1

HCID 86669071HCID 86669071, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-[2-(2,6-dichloro-phenyl)-cyclopropyl]-ethanone O-methyl-oxime (300 mg, 1.16 mmol), prepared as described in example P22, in ethanol (2 ml) and acetic acid (1 ml) was treated at ambient temperature with sodium cyanoborohydride (144 mg, 2.32 mmol) added in one portion. The resulting solution was stirred at ambient temperature for 10 hours. The solvent was evaporated under reduced pressure (co-evaporation with toluene twice) and the residue was slurried with 1 M NaOH (15 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 (15 g) (eluent: c-hexane/ethyl acetate 3:1). 260 mg (89.0% of theory) of trans-N-{1-[2-(2,6-dichlorophenyl)-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 (15 g) (eluent: c-hexane/ethyl acetate 3:1)
  8. addition260 mg (89.0% of theory) of trans-N-{1-[2-(2,6-dichlorophenyl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine as a mixture of diastereomeres
  9. customwas obtained in form of a clear liquid

Sources & evidence

ORD record
ord-89b5fe98a398434ca330144fcc199ca9
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Reaction notes

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