Water → (+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexylamine

HRID 2307104Notes

Reaction equation

HRID 2307104 reaction equation
[BH4-].[Na+].[CH3:3][O:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][O:15][CH3:16])[CH:10]=[CH:9][C:8]=1[CH:17]1[CH2:22][CH2:21][CH2:20][C:19](=[N:23]O)[CH2:18]1.O>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:3][O:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][O:15][CH3:16])[CH:10]=[CH:9][C:8]=1[CH:17]1[CH2:22][CH2:21][CH2:20][CH:19]([NH2:23])[CH2:18]1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86586318(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanone oxime

Product 1

HCID 22337808(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexylamineYield 65%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

Nickel chloride hexahydrate (77 mg) and sodium borohydride (24 mg) were added to a stirred solution of (±)-3-[2,4-bis(methoxymethoxy)phenyl]cyclohexanone oxime (50 mg) in methanol (2 ml). After 0.5 hr, water was added until effervescence ceased, the reaction mixture was filtered, and the residue was washed thoroughly with methanol. The combined filtrate and washings were evaporated in vacuo and the crude residue was purified by flash column chromatography (SiO2, dichloromethane/methanol, 9:1 v/v) to furnish the title compound as a colourless oil (31 mg, 65%) and a mixture of diastereoisomers; m/z (ES+) 295 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe residue was washed thoroughly with methanol
  3. customThe combined filtrate and washings were evaporated in vacuo
  4. customthe crude residue was purified by flash column chromatography (SiO2, dichloromethane/methanol, 9:1 v/v)

Sources & evidence

ORD record
ord-d0972a0d47fc4b0f98d7b14580ce9ee1
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

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