2-Amino-2-phenylethan-1-ol → HCID 20800573, compound

HRID 1071517Notes

Reaction equation

HRID 1071517 reaction equation
O[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:11])[CH:9]=2)[C:4](=[O:12])[O:3]1.[CH:13]1[CH:18]=[CH:17][C:16]([C@H:19]([NH2:22])[CH2:20]O)=[CH:15][CH:14]=1.CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:11][C:8]1[CH:9]=[C:10]2[C:5]([C:4](=[O:12])[N:22]3[CH:19]([C:16]4[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=4)[CH2:20][O:3][CH:2]32)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1347972-Amino-2-phenylethan-1-olHCID 151906771(3H)-Isobenzofuranone,3-hydroxy-5-methyl-(9CI)HCID 21226206Ethyl acetate hexane

Product 1

HCID 20800573HCID 20800573, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-hydroxy-5-methyl-3H-isobenzofuran-1-one (4.66 g, 28.39 mmol) and H-phenylglycinol (3.89 g, 28.39 mmol) was taken up in dry toluene and heated to reflux under argon for 12 h. The water generated was collected in a Dean-Stark trap. The reaction mixture was cooled to room temp and poured into 1N HCl and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate, water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (4:1 hexane/ethyl acetate) Yield 5.20 g.

Workup

  1. temperatureheated
  2. temperatureto reflux under argon for 12 h
  3. customThe water generated was collected in a Dean-Stark trap
  4. additionpoured into 1N HCl
  5. extractionthe aqueous layer was extracted three times with ethyl acetate
  6. washThe combined organic layers were washed with saturated sodium bicarbonate, water, brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe solution was filtered
  9. customthe solvent removed under reduced pressure
  10. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-b039f3d468b94ca2833fa7bbc6e8228a
Source dataset
uspto-grants-2005_06
Patent number
US06906067B2

Reaction notes

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