Sodium cyanoborohydride → HCID 58443678, compound

HRID 2381258Notes

Reaction equation

HRID 2381258 reaction equation
[CH3:1][O:2][N:3]=[C:4]([CH3:20])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH:4]([NH:3][O:2][CH3:1])[CH3:20])=[CH:7][CH:8]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 76787511HCID 76787511, compound

Product 1

HCID 58443678HCID 58443678, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
23 °C

Procedure

A solution of crude 1-[4-(4-chlorophenoxy)-phenyl]-propan-2-one O-methyl-oxime (6.0 g, 20.7 mmol) in acetic acid (50 ml) was treated at 10° C. with sodium cyanoborohydride (2.6 g, 41.4 mmol) added in small portions over 10 minutes and the resulting solution was stirred at 23° C. for 3.5 hours. The solvent was evaporated under reduced pressure (co-evaporation with toluene twice) and the residue was slurried with water and pH was adjusted to 11 with 1M NaOH. The aqueous phase was extracted with dichloromethane (2×20 ml), washed with brine and dried over anhydrous Na2SO4. After removal of the solvent (100 mbar; 45° C.), the residue (7.17 g) was purified by flash chromatography over silica gel (eluent: c-hexane). 3.91 g (65.0% of theory) of N-{2-[4-(4-chloro-phenoxy)-phenyl]-1-methyl-ethyl}-O-methyl-hydroxylamine was obtained in form of a clear liquid.

Workup

  1. additionadded in small portions over 10 minutes
  2. customThe solvent was evaporated under reduced pressure (co-evaporation with toluene twice) and the residue
  3. extractionThe aqueous phase was extracted with dichloromethane (2×20 ml)
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customAfter removal of the solvent (100 mbar; 45° C.)
  7. customthe residue (7.17 g) was purified by flash chromatography over silica gel (eluent: c-hexane)

Sources & evidence

ORD record
ord-561c2a29cce84136bf92c771f9e86f13
Source dataset
uspto-grants-2012_09
Patent number
US08258169B2

Reaction notes

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