Ethanolamine → HCID 57699419, 화합물

HRID 1670461노트

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HRID 1670461 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 57699419HCID 57699419, 화합물수율 100%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ec541de9cfe04d828ec2bea9941ffaa7
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994166B2

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