Ethyl Acetate → o-Amino-alpha-cyclopropylbenzyl alcohol

HRID 128531Notes

Reaction equation

HRID 128531 reaction equation
[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH2:12])=[O:5])[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>O1CCCC1>[NH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:4]([OH:5])[CH:1]1[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10931741(2-Aminophenyl)(cyclopropyl)methanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 15278634o-Amino-alpha-cyclopropylbenzyl alcoholYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of o-aminophenyl cyclopropyl ketone (7.78 g, 48.3 mmol) in tetrahydrofuran at 0° C. is added 29 mL of a 1.0M lithium aluminum hydride solution in tetrahydrofuran. The reaction mixture is stirred at 0° C. for 2 hours, warmed to and stirred at room temperature for 16 hours, quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and 30% to 50% ethyl acetate in hexanes solutions gives the title product as a yellow solid (5.02 g, 64%, mp 76°-79° C.) which is identified by 1HNMR and MS spectral analyses.

Workup

  1. temperaturewarmed to and
  2. stirringstirred at room temperature for 16 hours
  3. customquenched with saturated ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue

Sources & evidence

ORD record
ord-24e3e94c9f7a4f0e94de01d16f384bca
Source dataset
uspto-grants-1995_11
Patent number
US05464808

Reaction notes

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