Ammonium Chloride → HCID 69432581, compound

HRID 1269958Notes

Reaction equation

HRID 1269958 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([CH:9]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH2:10]1)([N+:6]([O-:8])=[O:7])[CH3:5].[Cl-].[NH4+]>CO>[CH3:5][C:4]([C@@H:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([OH:15])[CH2:10]1)([N+:6]([O-:8])=[O:7])[CH3:3].[CH3:5][C:4]([C@H:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([OH:15])[CH2:10]1)([N+:6]([O-:8])=[O:7])[CH3:3]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 10997733HCID 10997733, compound

Product 2

HCID 69431102HCID 69431102, compoundYield 15%HCID 69432581HCID 69432581, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere, sodium borohydride (343 mg, 9.07 mmol) was added to a solution of 3-(1-methyl-1-nitroethyl)cyclohexanone (1.68 g, 9.07 mmol) known in literature in methanol (17 ml) at 0° C. After 45 minutes, a saturated aqueous ammonium chloride solution was added to the reaction solution and then the methanol was concentrated under reduced pressure. The resulting aqueous solution was diluted with water and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain cis-3-(1-methyl-1-nitroethyl)cyclohexanol (499.1 mg, 29%), trans-3-(1-methyl-1-nitroethyl)cyclohexanol (259.6 mg, 15%) and a mixture of the isomers (55%).

Workup

  1. concentrationthe methanol was concentrated under reduced pressure
  2. additionThe resulting aqueous solution was diluted with water
  3. extractionextracted with chloroform
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customThe organic layer dried
  6. concentrationwas concentrated under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-56cc472c19214d43a499ea0b8d6610d9
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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