Ethanolamine → HCID 57699419、化合物

HRID 77293ノート

反応式

HRID 77293 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 57699419HCID 57699419、化合物収率 100%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6694b905d3e14b5f8b6ac339eb25d977
出典データセット
uspto-grants-2014_09
特許番号
US08841282B2

反応ノート

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