Octopamine → 2-[4-[2-[(beta,4-Dihydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one

HRID 465420

反応式

HRID 465420 の反応式
[Na].[CH:2]1[C:7]([CH:8]([OH:11])[CH2:9][NH2:10])=[CH:6][CH:5]=[C:4]([OH:12])[CH:3]=1.[CH2:13]([C:17]1[CH:32]=[CH:31][C:20]([O:21][CH2:22][C:23]2[O:24][CH:25]=[C:26]([OH:30])[C:27](=[O:29])[CH:28]=2)=[CH:19][CH:18]=1)[C:14]([CH3:16])=O.C([BH3-])#N.[Na+]>CO>[OH:11][CH:8]([C:7]1[CH:6]=[CH:5][C:4]([OH:12])=[CH:3][CH:2]=1)[CH2:9][NH:10][CH:14]([CH3:16])[CH2:13][C:17]1[CH:18]=[CH:19][C:20]([O:21][CH2:22][C:23]2[O:24][CH:25]=[C:26]([OH:30])[C:27](=[O:29])[CH:28]=2)=[CH:31][CH:32]=1

参加物

6

反応物 4

HCID 4581OctopamineHCID 5003444Sodium cyanoborohydrideHCID 5360545SodiumHCID 198745552-(4-acetonylphenoxymethyl)-5-hydroxy-4H-pyran-4-one

生成物 1

HCID 198745762-[4-[2-[(beta,4-Dihydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of the sodium salt of octopamine (0.65 g), and 2-(4-acetonylphenoxymethyl)-5-hydroxy-4H-pyran-4-one (1.0 g) in methanol was treated with sodium cyanoborohydride (0.3 g) and stirred at ambient temperature for 18 hours. The solvent was evaporated in vacuo. The residue was suspended in acetone and filtered, washed with acetone and then purified by column chromatography on silica using 5% methanol:chloroform as eluent-increasing to 15% methanol:chloroform after elution of fast-running impurities. This gave 2-[4-[2-[(β,4-dihydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one(0.4 g) as a (50:50) mixture of diastereoisomers.

後処理

  1. customThe solvent was evaporated in vacuo
  2. filtrationfiltered
  3. washwashed with acetone
  4. custompurified by column chromatography on silica using 5% methanol
  5. temperaturechloroform as eluent-increasing to 15% methanol
  6. washchloroform after elution of fast-running impurities
  7. additionThis gave 2-[4-[2-[(β,4-dihydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one(0.4 g) as a (50:50) mixture of diastereoisomers

出典と根拠

ORDレコード
ord-b42fdd0cf6e3484389763f6ba5052292
出典データセット
uspto-grants-1992_10
特許番号
US05153210

関連ノート

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