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

HRID 465420

반응식

HRID 465420 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b42fdd0cf6e3484389763f6ba5052292
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153210

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