Potassium Hydroxide → 1-(2-Aminophenyl)-3-cyclopropylcyclobutanol

HRID 2240483Notes

Reaction equation

HRID 2240483 reaction equation
[CH:1]1([CH:4]2[CH2:7][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[NH:15]C=O)([OH:8])[CH2:5]2)[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:6]1([OH:8])[CH2:5][CH:4]([CH:1]2[CH2:2][CH2:3]2)[CH2:7]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86761115N-[2-(3-cyclopropyl-1-hydroxycyclobutyl)-phenyl]Formamide

Product 1

HCID 685847901-(2-Aminophenyl)-3-cyclopropylcyclobutanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a sulfonation flask, a mixture consisting of 2.5 g (0.0108 mol) N-[2-(3-cyclopropyl-1-hydroxy-cyclobutyl)phenyl]-formamide (prepared as described in Example 8), 1.4 g (0.021 mol) potassium hydroxide and 25 ml methanol was stirred at reflux temperature for 4 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 crude material was purified by flash chromatography over silica gel (eluant: hexane/ethylacetate 1:1). Yield: 1.65 g (75% of theory) of 1-(2-aminophenyl)-3-cyclopropylcyclobutanol in the form of a slightly brownish solid (mp.: 58-61° C.).

Workup

  1. temperatureat reflux temperature for 4 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 crude material was purified by flash chromatography over silica gel (eluant: hexane/ethylacetate 1:1)

Sources & evidence

ORD record
ord-9a47e997e5ca41b48e2ec393098128c1
Source dataset
uspto-grants-2010_05
Patent number
US07723371B2

Reaction notes

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