Potassium Hydroxide → 1-(2-Aminophenyl)-2-cyclopropylcyclobutanol

HRID 2240479Notes

Reaction equation

HRID 2240479 reaction equation
[CH:1]1([CH:4]2[CH2:7][CH2:6][C:5]2([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15]C=O)[OH:8])[CH2:3][CH2:2]1.[OH-].[K+]>CO>[NH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:5]1([OH:8])[CH2:6][CH2:7][CH:4]1[CH:1]1[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86628157N-[2-(2-cyclopropyl-1-hydroxycyclobutyl)-phenyl]Formamide

Product 1

HCID 685838271-(2-Aminophenyl)-2-cyclopropylcyclobutanolYield 81.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a sulfonation flask, a mixture consisting of 3.35 g (0.0145 mol) N-[2-(2-cyclopropyl-1-hydroxycyclobutyl)phenyl]-formamide (prepared as described in Example 3), 1.3 g (0.02 mol) potassium hydroxide and 25 ml methanol was stirred at reflux temperature for 3 hours. Then the solvent was distilled off in a water jet vacuum and the residue taken up in 100 ml of ethyl acetate. The organic phase was washed three times with water and after drying with sodium sulphate the solvent was distilled off in a water jet vacuum. The raw material was purified by flash chromatography over silica gel (eluant: hexane/ethyl acetate 2:1). Yield: 2.4 g (80% of theory) of 1-(2-aminophenyl)-2-cyclopropylcyclobutanol in the form of a slightly brownish oil (1HNMR (CDCl3): 0.2-0.36 ppm/m/2H, 0.55 ppm/m/2H), 1.08 ppm/m/1H), 1.81 ppm/m/2H, 2.3-2.48 ppm/m/3H, 4.2 ppm (broad)/3H−NH2+OH), 6.6-6.72 ppm/m/2H, 7.05-7.15/m/2H− only one isomer obtained).).

Workup

  1. temperatureat reflux temperature for 3 hours
  2. distillationThen the solvent was distilled off in a water jet vacuum
  3. washThe organic phase was washed three times with water
  4. dry with materialafter drying with sodium sulphate the solvent
  5. distillationwas distilled off in a water jet vacuum
  6. customThe raw material was purified by flash chromatography over silica gel (eluant: hexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-0d1ab33b68ea4bad90b90531618e796b
Source dataset
uspto-grants-2010_05
Patent number
US07723371B2

Reaction notes

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