Ethanol → HCID 13020601, compound

HRID 1680883Notes

Reaction equation

HRID 1680883 reaction equation
C(O)(=O)C(O)=O.[CH3:7][C:8]([NH:21][CH2:22][CH:23]([OH:38])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([CH3:20])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.C(O)C>[H][H].[C].[Pd]>[CH3:20][C:8]([NH:21][CH2:22][CH:23]([OH:38])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([CH3:7])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 23454858HCID 23454858, compound

Product 1

HCID 13020601HCID 13020601, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 178418361HCID 178418361, compoundSolvent2×

Procedure

A mixture of 263 mg of α-[(α,α-dimethyl-3,4-dimethoxyphenethylamino)methyl]-2-benzyloxybenzylalcohol oxalate (M.p. 157°-158° C.), 150 mg of 10% palladium-carbon and 15 ml of 95% aqueous ethanol is shaken at 20° C. in hydrogen gas atmosphere under atmospheric pressure. After the uptake of hydrogen is completed, insoluble materials are removed by filtration. The filtrate is evaporated to remove the solvent. The residue (colorless oil) is crystallized with a mixture of acetone and ether, and then recrystallized from isopropylalcohol. 180 mg of α-[(α,α-dimethyl-3,4-dimethoxyphenethylamino)methyl]-2-hydroxybenzylalcohol 1/2 oxalate are thereby obtained as colorless prisms.

Workup

  1. custominsoluble materials are removed by filtration
  2. customThe filtrate is evaporated
  3. customto remove the solvent
  4. customThe residue (colorless oil) is crystallized with a mixture of acetone and ether
  5. customrecrystallized from isopropylalcohol

Sources & evidence

ORD record
ord-9289ffa3b8084446a86c82d6eec228c0
Source dataset
uspto-grants-1981_06
Patent number
US04276304

Reaction notes

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