Dimethylamine → 2-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-6-dimethylaminomethyl-4H-pyran-4-one

HRID 465423ノート

反応式

HRID 465423 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH:5]([OH:27])[CH2:6][NH:7][CH:8]([CH3:26])[CH2:9][C:10]1[CH:25]=[CH:24][C:13]([O:14][CH2:15][C:16]2[O:17][CH:18]=[C:19]([OH:23])[C:20](=[O:22])[CH:21]=2)=[CH:12][CH:11]=1.[CH3:31][NH:32][CH3:33].[CH2:34]=O>C(O)C.C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH:5]([OH:27])[CH2:6][NH:7][CH:8]([CH3:26])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][C:16]2[O:17][C:18]([CH2:31][N:32]([CH3:34])[CH3:33])=[C:19]([OH:23])[C:20](=[O:22])[CH:21]=2)=[CH:24][CH:25]=1

参加物

6

反応物 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 198745272-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one

生成物 1

HCID 198745062-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-6-dimethylaminomethyl-4H-pyran-4-one

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 19096565Water ethanol溶媒

実験手順

A solution of 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one 0.8 g) in ethanol, was added to a mixture of dimethylamine (0.28 ml of a 33% solution, in ethanol) and formaldehyde (0.175 ml of a 37% aq. solution) in ethanol:water (95:5), (50 ml), at room temperature and allowed to stand for 1h. The solvent was evaporated in vacuo, the residue was partitioned between ethyl acetate and water separated and the organic extracts dried (magnesium sulphate), filtered and evaporated to an oil which was chromatographed on silica. Elution with chloroform: methanol (95:5) gave 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-6-dimethylaminomethyl-4H-pyran-4-one (0.4 g) as a 49:51 mixture of diastereoisomers.

後処理

  1. customat room temperature
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. customseparated
  5. dry with materialthe organic extracts dried (magnesium sulphate)
  6. filtrationfiltered
  7. customevaporated to an oil which
  8. customwas chromatographed on silica
  9. washElution with chloroform: methanol (95:5)

出典と根拠

ORDレコード
ord-99854ab73eda4a74a63280b14a8960e4
出典データセット
uspto-grants-1992_10
特許番号
US05153210

反応ノート

読み込み中…