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

HRID 465420

Reaction equation

HRID 465420 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b42fdd0cf6e3484389763f6ba5052292
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Linked notes

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