Ethanolamine → HCID 57699419, compound

HRID 77293Notes

Reaction equation

HRID 77293 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[Cl:5][C:6]1[CH:7]=[C:8]([C@@H:13]2[CH2:15][O:14]2)[CH:9]=[CH:10][C:11]=1[Cl:12]>C(O)(C)C>[Cl:5][C:6]1[CH:7]=[C:8]([C@@H:13]([OH:14])[CH2:15][NH:4][CH2:3][CH2:1][OH:2])[CH:9]=[CH:10][C:11]=1[Cl:12]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 10352473(2R)-2-(3,4-dichlorophenyl)oxirane

Product 1

HCID 57699419HCID 57699419, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a 3 neck flask equipped with a mechanical stirrer, thermocouple and addition funnel in an ambient temperature water bath was added ethanolamine (330 mL, 5.47 mol). (R)-2-(3,4-dichlorophenyl)oxirane (184 g, 976 mmol) in isopropanol (75 mL) was added dropwise over 1 h. Reaction temperature stayed <30° C. during addition. The reaction mixture was stirred at ambient temperature for 14 h, diluted with 2000 mL of ice water and extracted three times with 1000 mL of ethyl acetate. The combined organic phases were dried over MgSO4, filtered over Celite and concentrated in vacuo affording (1R)-1-(3,4-dichlorophenyl)-2-(2-hydroxyethylamino)-ethanol (244 g, 100%) as a white semi-solid. 1H-NMR (400 MHz, CDCl3) δ 7.58-7.54 (m, 2H), 7.35-7.32 (m, 1H), 5.51 (s, 1H), 4.64 (dd, J=5.0, 7.2 Hz, 1H), 4.49 (s, 1H), 3.43 (dd, J=5.0, 10.4 Hz, 2H), 2.69-2.50 (m, 4H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=250.3; tR=0.84 min.

Workup

  1. customIn a 3 neck flask equipped with a mechanical stirrer
  2. additionthermocouple and addition funnel in an ambient temperature water bath
  3. customReaction temperature
  4. additionstayed <30° C. during addition
  5. extractionextracted three times with 1000 mL of ethyl acetate
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. filtrationfiltered over Celite
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6694b905d3e14b5f8b6ac339eb25d977
Source dataset
uspto-grants-2014_09
Patent number
US08841282B2

Reaction notes

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