Sodium cyanoborohydride → HCID 58443694, compound

HRID 2381263Notes

Reaction equation

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

Participants

Conditions

Temperature: 24 °C

Procedure

A solution of 2-(2,4-dichlorophenyl)-pentanal O-methyl-oxime (6.0 g, 23 mmol) in acetic acid (50 ml) was treated at 10° C. with sodium cyanoborohydride (2.90 g, 46 mmol) added in small portions over 10 minutes and the resulting solution was stirred at 24° C. for 4 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 (2×50 ml), washed with brine and dried over anhydrous Na2SO4. After removal of the solvent (100 mbar; 45° C.), the residue (6.2 g) was purified by flash chromatography over silica gel (250 g; eluent: c-hexane). 5.15 g (79.0% of theory) of N-[2-(2,4-dichlorophenyl)-pentyl]-O-methyl-hydroxylamine was obtained in form of a clear liquid.

Workup

additionadded in small portions over 10 minutes
customThe solvent was evaporated under reduced pressure (co-evaporation with toluene twice) and the residue
extractionThe aqueous phase was extracted with dichloromethane (2×50 ml)
washwashed with brine
dry with materialdried over anhydrous Na2SO4
customAfter removal of the solvent (100 mbar; 45° C.)
customthe residue (6.2 g) was purified by flash chromatography over silica gel (250 g; eluent: c-hexane)

Sources & evidence

ORD record: ord-ca16df1dc5b047a0b386229143c3ef03
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258169B2

Reaction notes

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